CA1304188C - Crosslinked gels based on glycol esters of methacrylic acid with the enhanced swelling capacity in water and a method for producing thereof - Google Patents
Crosslinked gels based on glycol esters of methacrylic acid with the enhanced swelling capacity in water and a method for producing thereofInfo
- Publication number
- CA1304188C CA1304188C CA000531363A CA531363A CA1304188C CA 1304188 C CA1304188 C CA 1304188C CA 000531363 A CA000531363 A CA 000531363A CA 531363 A CA531363 A CA 531363A CA 1304188 C CA1304188 C CA 1304188C
- Authority
- CA
- Canada
- Prior art keywords
- gel
- water
- swelling
- swelling capacity
- esters
- 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 - Lifetime
Links
- 230000008961 swelling Effects 0.000 title claims abstract description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 27
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 7
- 239000000499 gel Substances 0.000 title abstract description 20
- 150000002334 glycols Chemical class 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims abstract description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 10
- 239000011780 sodium chloride Substances 0.000 claims abstract description 9
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims abstract description 8
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 4
- 229940044192 2-hydroxyethyl methacrylate Drugs 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 8
- 239000012670 alkaline solution Substances 0.000 claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 5
- 238000007334 copolymerization reaction Methods 0.000 claims description 4
- 239000003431 cross linking reagent Substances 0.000 claims description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
- 230000009471 action Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 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 claims 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract description 5
- 230000003247 decreasing effect Effects 0.000 abstract description 2
- 230000004048 modification Effects 0.000 abstract description 2
- 238000012986 modification Methods 0.000 abstract description 2
- 238000005406 washing Methods 0.000 abstract description 2
- 238000003780 insertion Methods 0.000 abstract 1
- 230000037431 insertion Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000008521 reorganization Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OLQFXOWPTQTLDP-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCO OLQFXOWPTQTLDP-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 210000001584 soft palate Anatomy 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 210000001519 tissue Anatomy 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
- C08F8/00—Chemical modification by after-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Eyeglasses (AREA)
- Materials For Medical Uses (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS861552A CS256607B1 (en) | 1986-03-06 | 1986-03-06 | Cross-linked gels on base of metacrylic acid's glycoesters with increased swelling capacity in water and method of their production |
| CSPV1552-86 | 1986-03-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1304188C true CA1304188C (en) | 1992-06-23 |
Family
ID=5350159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000531363A Expired - Lifetime CA1304188C (en) | 1986-03-06 | 1987-03-06 | Crosslinked gels based on glycol esters of methacrylic acid with the enhanced swelling capacity in water and a method for producing thereof |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS62275148A (cs) |
| CA (1) | CA1304188C (cs) |
| CS (1) | CS256607B1 (cs) |
| DE (1) | DE3707177C2 (cs) |
| FR (1) | FR2595361B1 (cs) |
| GB (2) | GB8704689D0 (cs) |
| IT (1) | IT1203358B (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11339263B2 (en) | 2015-03-16 | 2022-05-24 | Shpp Global Technologies B.V. | Fibrillated polymer compositions and methods of their manufacture |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4914170A (en) * | 1987-11-17 | 1990-04-03 | Rohm And Haas Company | Superabsorbent polymeric compositions and process for producing the same |
| DE19623289B4 (de) * | 1996-06-11 | 2005-06-30 | Morcher Gmbh | Verwendung von Polymethylmethacrylat zur Herstellung eines Augenimplantats |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1467028A (fr) * | 1964-07-02 | 1967-01-27 | Ceskoslovenska Akademie Ved | Procédé pour la fabrication de lentilles de contact notamment en hydrogel faiblement réticulé, ainsi que les lentilles conformes à celles obtenues par le présent procédé ou procédé similaire |
| US3803093A (en) * | 1971-02-25 | 1974-04-09 | C Neefe | Methyl methacrylate copolymer which may be hydrated |
| US3951528A (en) * | 1971-06-02 | 1976-04-20 | Patent Structures, Inc. | Method of making polymeric contact lens |
| CS163469B1 (cs) * | 1972-05-22 | 1975-09-15 | ||
| 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 |
| US3963685A (en) * | 1974-05-13 | 1976-06-15 | Abrahams Robert A | Alcohol soluble hydrophilic polymer via aqueous polymerization |
| JPS52102748A (en) * | 1976-02-25 | 1977-08-29 | Hoya Lens Co Ltd | Method of manufacturing soft contact lens |
| GB2036765B (en) * | 1978-11-30 | 1983-01-19 | Global Vision Ltd | Soft contact lenses |
| CA1184367A (en) * | 1981-06-22 | 1985-03-26 | Novartis Ag | Process for producing shaped articles having improved surfaces |
| EP0166051B1 (en) * | 1984-06-28 | 1989-03-15 | Ceskoslovenska akademie ved | Process for fabricating an intraocular lens |
-
1986
- 1986-03-06 CS CS861552A patent/CS256607B1/cs not_active IP Right Cessation
-
1987
- 1987-02-27 GB GB878704689A patent/GB8704689D0/en active Pending
- 1987-03-05 GB GB8705097A patent/GB2188051B/en not_active Expired - Lifetime
- 1987-03-05 IT IT19599/87A patent/IT1203358B/it active
- 1987-03-06 DE DE3707177A patent/DE3707177C2/de not_active Expired - Fee Related
- 1987-03-06 CA CA000531363A patent/CA1304188C/en not_active Expired - Lifetime
- 1987-03-06 FR FR8703106A patent/FR2595361B1/fr not_active Expired - Fee Related
- 1987-03-06 JP JP62050409A patent/JPS62275148A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11339263B2 (en) | 2015-03-16 | 2022-05-24 | Shpp Global Technologies B.V. | Fibrillated polymer compositions and methods of their manufacture |
Also Published As
| Publication number | Publication date |
|---|---|
| CS155286A1 (en) | 1987-09-17 |
| FR2595361A1 (fr) | 1987-09-11 |
| DE3707177C2 (de) | 1997-06-05 |
| DE3707177A1 (de) | 1987-09-10 |
| JPS62275148A (ja) | 1987-11-30 |
| GB8704689D0 (en) | 1987-04-01 |
| FR2595361B1 (fr) | 1993-02-19 |
| GB2188051A (en) | 1987-09-23 |
| GB8705097D0 (en) | 1987-04-08 |
| IT1203358B (it) | 1989-02-15 |
| CS256607B1 (en) | 1988-04-15 |
| IT8719599A0 (it) | 1987-03-05 |
| GB2188051B (en) | 1990-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |