DE2503755A1 - Hydrogel-copolymer, insbesondere zur herstellung von kontaktlinsen - Google Patents
Hydrogel-copolymer, insbesondere zur herstellung von kontaktlinsenInfo
- Publication number
- DE2503755A1 DE2503755A1 DE19752503755 DE2503755A DE2503755A1 DE 2503755 A1 DE2503755 A1 DE 2503755A1 DE 19752503755 DE19752503755 DE 19752503755 DE 2503755 A DE2503755 A DE 2503755A DE 2503755 A1 DE2503755 A1 DE 2503755A1
- Authority
- DE
- Germany
- Prior art keywords
- cross
- hydrogel
- linked
- mema
- terpolymer
- 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.)
- Withdrawn
Links
- 239000000017 hydrogel Substances 0.000 title claims description 18
- 229920001577 copolymer Polymers 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000000178 monomer Substances 0.000 claims description 27
- 229920000642 polymer Polymers 0.000 claims description 20
- 229920001897 terpolymer Polymers 0.000 claims description 20
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 11
- 239000011230 binding agent Substances 0.000 claims description 11
- 239000000499 gel Substances 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 239000003431 cross linking reagent Substances 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 239000002504 physiological saline solution Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 235000011187 glycerol Nutrition 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 230000009257 reactivity Effects 0.000 claims description 3
- PSYOUKJKRMXYOB-UHFFFAOYSA-N 2-methyl-n-(2-phenoxyethyl)prop-2-enamide Chemical compound CC(=C)C(=O)NCCOC1=CC=CC=C1 PSYOUKJKRMXYOB-UHFFFAOYSA-N 0.000 claims description 2
- LKQALBVIAWZTAK-UHFFFAOYSA-N [2-hydroxy-3-[(2-methylpropan-2-yl)oxy]propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)COC(C)(C)C LKQALBVIAWZTAK-UHFFFAOYSA-N 0.000 claims description 2
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005399 allylmethacrylate group Chemical group 0.000 claims 1
- 239000007767 bonding agent Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 13
- 229910052760 oxygen Inorganic materials 0.000 description 13
- 239000001301 oxygen Substances 0.000 description 13
- 230000035699 permeability Effects 0.000 description 13
- 238000010521 absorption reaction Methods 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 3
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 3
- -1 unsaturated aliphatic radicals Chemical class 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- BMCVSUCDMJFKSZ-UHFFFAOYSA-N (2-hydroxy-3-methoxypropyl) 2-methylprop-2-enoate Chemical compound COCC(O)COC(=O)C(C)=C BMCVSUCDMJFKSZ-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- PBGPBHYPCGDFEZ-UHFFFAOYSA-N 1-ethenylpiperidin-2-one Chemical compound C=CN1CCCCC1=O PBGPBHYPCGDFEZ-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- LKMJVFRMDSNFRT-UHFFFAOYSA-N 2-(methoxymethyl)oxirane Chemical compound COCC1CO1 LKMJVFRMDSNFRT-UHFFFAOYSA-N 0.000 description 1
- AGJBKFAPBKOEGA-UHFFFAOYSA-M 2-methoxyethylmercury(1+);acetate Chemical compound COCC[Hg]OC(C)=O AGJBKFAPBKOEGA-UHFFFAOYSA-M 0.000 description 1
- ILZXXGLGJZQLTR-UHFFFAOYSA-N 2-phenylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1 ILZXXGLGJZQLTR-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- 102100026735 Coagulation factor VIII Human genes 0.000 description 1
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 1
- 101100190537 Homo sapiens PNN gene Proteins 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 102100038374 Pinin Human genes 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 210000001519 tissue Anatomy 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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/282—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing two or more oxygen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Eyeglasses (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Medical Uses (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1408274 | 1974-03-29 | ||
| GB2975874 | 1974-07-04 | ||
| GB6018/75A GB1498426A (en) | 1974-11-22 | 1974-11-22 | Copolymer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2503755A1 true DE2503755A1 (de) | 1975-10-09 |
Family
ID=27257089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752503755 Withdrawn DE2503755A1 (de) | 1974-03-29 | 1975-01-30 | Hydrogel-copolymer, insbesondere zur herstellung von kontaktlinsen |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4022754A (en, 2012) |
| JP (1) | JPS50128740A (en, 2012) |
| AR (1) | AR208398A1 (en, 2012) |
| AT (1) | AT349788B (en, 2012) |
| CA (1) | CA1052945A (en, 2012) |
| DD (1) | DD119798A5 (en, 2012) |
| DE (1) | DE2503755A1 (en, 2012) |
| DK (1) | DK15575A (en, 2012) |
| ES (1) | ES434413A1 (en, 2012) |
| FI (1) | FI750315A7 (en, 2012) |
| FR (1) | FR2273019B1 (en, 2012) |
| IE (1) | IE40940B1 (en, 2012) |
| IL (1) | IL46514A (en, 2012) |
| NL (1) | NL7501280A (en, 2012) |
| NO (1) | NO750199L (en, 2012) |
| SE (1) | SE7501203L (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0234749A3 (en) * | 1986-01-28 | 1988-11-17 | Smith And Nephew Associated Companies P.L.C. | Hydrogel polymers |
| EP0350030A3 (en) * | 1988-07-08 | 1990-07-18 | Ceskoslovenska Akademie Ved | Hydrophilic copolymers, process for their preparation and their use |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2511841A (en) * | 1950-06-20 | Windrowing device | ||
| FR2402525A1 (fr) * | 1977-09-12 | 1979-04-06 | Toray Industries | Procede de fabrication de compositions de lentilles de contact molles et nouveaux produits ainsi obtenus |
| JPS5455455A (en) * | 1977-10-12 | 1979-05-02 | Toyo Contact Lens Co Ltd | Contact lens |
| JPS5466853A (en) * | 1977-11-08 | 1979-05-29 | Toyo Contact Lens Co Ltd | Soft contact lens |
| US4182802A (en) * | 1977-12-27 | 1980-01-08 | Samuel Loshaek | Hydrophilic polymers and contact lenses of high water content |
| USRE31422E (en) * | 1977-12-27 | 1983-10-18 | Schering Corporation | Hydrophilic polymers and contact lenses of high water content |
| US4328148A (en) * | 1979-07-27 | 1982-05-04 | Petr Kuzma | Compositions comprising water and hydrophilic polymers and contact lenses therefrom |
| US4436887A (en) | 1981-11-12 | 1984-03-13 | Bausch & Lomb Incorporated | N-Vinyl lactam based biomedical devices |
| CA1272329C (en) * | 1985-01-09 | 1990-07-31 | HIGHLY HYGROSCOPIC SOFT CONTACT LENSES | |
| US4620954A (en) * | 1985-06-07 | 1986-11-04 | Ciba Vision Care Corp. | Hydrogel from ultraviolet-initiated copolymerization |
| SE9403392D0 (sv) * | 1994-10-06 | 1994-10-06 | Pharmacia Ab | Intraocular lens materials |
| US20060229423A1 (en) * | 2005-03-17 | 2006-10-12 | Parakka James P | Process for the production of monodisperse and narrow disperse monofunctional silicones |
| CN102159704B (zh) * | 2008-01-30 | 2013-12-25 | 杰龙公司 | 用于在化学成分确定的培养基中培养细胞的合成表面 |
| KR20110005682A (ko) | 2008-01-30 | 2011-01-18 | 제론 코포레이션 | 줄기 세포 유래 심근세포 배양용 합성 표면 |
| CN101939362A (zh) | 2008-01-30 | 2011-01-05 | 杰龙公司 | 用于培养干细胞衍生的少突胶质细胞前体细胞的合成表面 |
| US7939579B1 (en) * | 2008-07-09 | 2011-05-10 | Contamac Limited | Hydrogels and methods of manufacture |
| US8440738B2 (en) | 2008-07-09 | 2013-05-14 | Timothy Higgs | Silicone hydrogels and methods of manufacture |
| JP7050630B2 (ja) | 2018-08-30 | 2022-04-08 | 信越化学工業株式会社 | （メタ）アクリロイル化合物及びその製造方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3532679A (en) * | 1969-04-07 | 1970-10-06 | Robert Steckler | Hydrogels from cross-linked polymers of n-vinyl lactams and alkyl acrylates |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3780003A (en) * | 1968-10-22 | 1973-12-18 | Hydron Ltd | Polymers of alkoxy and hydroxy alkyl acrylates or methacrylates |
| US3639524A (en) * | 1969-07-28 | 1972-02-01 | Maurice Seiderman | Hydrophilic gel polymer insoluble in water from polyvinylpyrrolidone with n-vinyl-2-pyrrolidone and methacrylic modifier |
| US3784540A (en) * | 1971-10-05 | 1974-01-08 | Nat Patent Dev Corp | Process of preparing soluble hema-based polymers |
-
1975
- 1975-01-01 AR AR257548A patent/AR208398A1/es active
- 1975-01-21 DK DK15575*#A patent/DK15575A/da not_active Application Discontinuation
- 1975-01-23 NO NO750199A patent/NO750199L/no unknown
- 1975-01-27 CA CA218,673A patent/CA1052945A/en not_active Expired
- 1975-01-27 US US05/544,065 patent/US4022754A/en not_active Expired - Lifetime
- 1975-01-28 IL IL46514A patent/IL46514A/en unknown
- 1975-01-28 FR FR7502641A patent/FR2273019B1/fr not_active Expired
- 1975-01-30 DE DE19752503755 patent/DE2503755A1/de not_active Withdrawn
- 1975-01-31 AT AT71375A patent/AT349788B/de not_active IP Right Cessation
- 1975-02-03 ES ES434413A patent/ES434413A1/es not_active Expired
- 1975-02-04 NL NL7501280A patent/NL7501280A/xx not_active Application Discontinuation
- 1975-02-04 SE SE7501203A patent/SE7501203L/xx unknown
- 1975-02-05 JP JP50014455A patent/JPS50128740A/ja active Pending
- 1975-02-05 DD DD184021A patent/DD119798A5/xx unknown
- 1975-02-05 FI FI750315A patent/FI750315A7/fi not_active Application Discontinuation
- 1975-02-19 IE IE338/75A patent/IE40940B1/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3532679A (en) * | 1969-04-07 | 1970-10-06 | Robert Steckler | Hydrogels from cross-linked polymers of n-vinyl lactams and alkyl acrylates |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0234749A3 (en) * | 1986-01-28 | 1988-11-17 | Smith And Nephew Associated Companies P.L.C. | Hydrogel polymers |
| EP0350030A3 (en) * | 1988-07-08 | 1990-07-18 | Ceskoslovenska Akademie Ved | Hydrophilic copolymers, process for their preparation and their use |
Also Published As
| Publication number | Publication date |
|---|---|
| IL46514A (en) | 1977-08-31 |
| IE40940L (en) | 1975-09-29 |
| FI750315A7 (en, 2012) | 1975-09-30 |
| JPS50128740A (en, 2012) | 1975-10-11 |
| FR2273019A1 (en, 2012) | 1975-12-26 |
| ES434413A1 (es) | 1977-06-16 |
| CA1052945A (en) | 1979-04-17 |
| ATA71375A (de) | 1978-09-15 |
| US4022754A (en) | 1977-05-10 |
| NO750199L (en, 2012) | 1975-09-30 |
| DD119798A5 (en, 2012) | 1976-05-12 |
| AR208398A1 (es) | 1976-12-27 |
| SE7501203L (en, 2012) | 1975-09-30 |
| NL7501280A (nl) | 1975-10-01 |
| AU7785975A (en) | 1976-08-05 |
| FR2273019B1 (en, 2012) | 1978-07-13 |
| IE40940B1 (en) | 1979-09-12 |
| AT349788B (de) | 1979-04-25 |
| DK15575A (en, 2012) | 1975-09-30 |
| IL46514A0 (en) | 1975-04-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8136 | Disposal/non-payment of the fee for publication/grant |