CA2404522A1 - Verres de contact composes d'un melange sulfone fluoree-silicone-hydrogel, dispositifs optiques medicaux et compositions connexes - Google Patents
Verres de contact composes d'un melange sulfone fluoree-silicone-hydrogel, dispositifs optiques medicaux et compositions connexes Download PDFInfo
- Publication number
- CA2404522A1 CA2404522A1 CA002404522A CA2404522A CA2404522A1 CA 2404522 A1 CA2404522 A1 CA 2404522A1 CA 002404522 A CA002404522 A CA 002404522A CA 2404522 A CA2404522 A CA 2404522A CA 2404522 A1 CA2404522 A1 CA 2404522A1
- Authority
- CA
- Canada
- Prior art keywords
- sulfone
- acrylic
- monomer
- integer
- copolymer
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims description 28
- 230000003287 optical effect Effects 0.000 title description 4
- 239000000017 hydrogel Substances 0.000 title description 3
- 239000000178 monomer Substances 0.000 claims abstract description 51
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 24
- 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 17
- 150000002148 esters Chemical class 0.000 claims abstract description 17
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229920001577 copolymer Polymers 0.000 claims abstract description 9
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims abstract 3
- 229920001870 copolymer plastic Polymers 0.000 claims description 22
- -1 cyclic ester Chemical class 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 8
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 8
- 125000005395 methacrylic acid group Chemical class 0.000 claims description 7
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000003431 cross linking reagent Substances 0.000 claims description 5
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- VALVZMYXOGXJRP-UHFFFAOYSA-N (2-hydroxycyclohexyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1O VALVZMYXOGXJRP-UHFFFAOYSA-N 0.000 claims description 3
- WUIJTQZXUURFQU-UHFFFAOYSA-N 1-methylsulfonylethene Chemical compound CS(=O)(=O)C=C WUIJTQZXUURFQU-UHFFFAOYSA-N 0.000 claims description 3
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 claims description 3
- GWPLOKPTQDEXNA-UHFFFAOYSA-N 2-methylsulfonylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCS(C)(=O)=O GWPLOKPTQDEXNA-UHFFFAOYSA-N 0.000 claims description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 3
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 3
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 3
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 3
- ZPQFAVDVWVKUOJ-UHFFFAOYSA-N 1-ethenylsulfonylbutane Chemical compound CCCCS(=O)(=O)C=C ZPQFAVDVWVKUOJ-UHFFFAOYSA-N 0.000 claims description 2
- BJEWLOAZFAGNPE-UHFFFAOYSA-N 1-ethenylsulfonylethane Chemical compound CCS(=O)(=O)C=C BJEWLOAZFAGNPE-UHFFFAOYSA-N 0.000 claims description 2
- GKRDUERMXXKTEG-UHFFFAOYSA-N 1-ethenylsulfonylpentane Chemical compound CCCCCS(=O)(=O)C=C GKRDUERMXXKTEG-UHFFFAOYSA-N 0.000 claims description 2
- DBCLLYFDDUBSML-UHFFFAOYSA-N 1-ethenylsulfonylpropane Chemical compound CCCS(=O)(=O)C=C DBCLLYFDDUBSML-UHFFFAOYSA-N 0.000 claims description 2
- UFAVJQDLGJFYFY-UHFFFAOYSA-N 2-(benzenesulfonyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCS(=O)(=O)C1=CC=CC=C1 UFAVJQDLGJFYFY-UHFFFAOYSA-N 0.000 claims description 2
- DSOQNQBWSKFGJG-UHFFFAOYSA-N 2-[ethyl(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl)amino]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCN(CC)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F DSOQNQBWSKFGJG-UHFFFAOYSA-N 0.000 claims description 2
- ICMDXJQURWMJCS-UHFFFAOYSA-N 2-butylsulfonylethyl 2-methylprop-2-enoate Chemical compound CCCCS(=O)(=O)CCOC(=O)C(C)=C ICMDXJQURWMJCS-UHFFFAOYSA-N 0.000 claims description 2
- QQLBBMXUMAPIEQ-UHFFFAOYSA-N 2-ethenylsulfonylethoxybenzene Chemical compound C=CS(=O)(=O)CCOC1=CC=CC=C1 QQLBBMXUMAPIEQ-UHFFFAOYSA-N 0.000 claims description 2
- FHPGUDZEMVTLRC-UHFFFAOYSA-N 2-ethylsulfonylethyl 2-methylprop-2-enoate Chemical compound CCS(=O)(=O)CCOC(=O)C(C)=C FHPGUDZEMVTLRC-UHFFFAOYSA-N 0.000 claims description 2
- KAIOBIMIFKUTKB-UHFFFAOYSA-N 2-pentylsulfonylethyl 2-methylprop-2-enoate Chemical compound CCCCCS(=O)(=O)CCOC(=O)C(C)=C KAIOBIMIFKUTKB-UHFFFAOYSA-N 0.000 claims description 2
- PDJRFRQHLPDXNB-UHFFFAOYSA-N 2-propylsulfonylethyl 2-methylprop-2-enoate Chemical compound CCCS(=O)(=O)CCOC(=O)C(C)=C PDJRFRQHLPDXNB-UHFFFAOYSA-N 0.000 claims description 2
- JHGHTBSOZYDUJC-UHFFFAOYSA-N ethenylsulfonylcyclohexane Chemical compound C=CS(=O)(=O)C1CCCCC1 JHGHTBSOZYDUJC-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000010348 incorporation Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 239000000975 dye Substances 0.000 claims 1
- 230000000887 hydrating effect Effects 0.000 claims 1
- 229920001477 hydrophilic polymer Polymers 0.000 claims 1
- 239000000049 pigment Substances 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- 150000004040 pyrrolidinones Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 8
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 7
- 230000036571 hydration Effects 0.000 description 5
- 238000006703 hydration reaction Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 4
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 3
- 229940044192 2-hydroxyethyl methacrylate Drugs 0.000 description 3
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 3
- 229910018557 Si O Inorganic materials 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 1
- DULAHVOOPMNHFB-UHFFFAOYSA-N 2-[ethyl(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl)amino]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN(CC)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F DULAHVOOPMNHFB-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- SQNSFOLJSDCSLZ-UHFFFAOYSA-N [O].C(=C)N1C(CCC1)=O Chemical compound [O].C(=C)N1C(CCC1)=O SQNSFOLJSDCSLZ-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000882 contact lens solution Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011953 free-radical catalyst Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- 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
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
-
- 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
- C08F220/38—Esters containing sulfur
- C08F220/387—Esters containing sulfur and containing nitrogen and oxygen
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Eyeglasses (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002404522A CA2404522A1 (fr) | 2002-09-19 | 2002-09-19 | Verres de contact composes d'un melange sulfone fluoree-silicone-hydrogel, dispositifs optiques medicaux et compositions connexes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002404522A CA2404522A1 (fr) | 2002-09-19 | 2002-09-19 | Verres de contact composes d'un melange sulfone fluoree-silicone-hydrogel, dispositifs optiques medicaux et compositions connexes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2404522A1 true CA2404522A1 (fr) | 2004-03-19 |
Family
ID=32075098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002404522A Abandoned CA2404522A1 (fr) | 2002-09-19 | 2002-09-19 | Verres de contact composes d'un melange sulfone fluoree-silicone-hydrogel, dispositifs optiques medicaux et compositions connexes |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2404522A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007147599A1 (fr) * | 2006-06-21 | 2007-12-27 | Acri.Tec Ag Gesellschaft Für Ophtalmotologische Producte | Composition ophtalmologique et son utilisation |
-
2002
- 2002-09-19 CA CA002404522A patent/CA2404522A1/fr not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007147599A1 (fr) * | 2006-06-21 | 2007-12-27 | Acri.Tec Ag Gesellschaft Für Ophtalmotologische Producte | Composition ophtalmologique et son utilisation |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |