CS257979B1 - Hydrophilic copolymer and method of its production - Google Patents

Hydrophilic copolymer and method of its production Download PDF

Info

Publication number: CS257979B1
Authority: CS; Czechoslovakia
Prior art keywords: mixture; water; glycol dimethacrylate; weight; hydroxyethoxy
Prior art date: 1986-06-24

Application number

CS864639A

Other languages

Czech (cs)

English (en)

Inventor

Otto Wichterle

Jiri Vacik

Jiri Michalek

Zuzana Krcova

Jiri Vodnansky

Original Assignee

Otto Wichterle

Jiri Vacik

Jiri Michalek

Zuzana Krcova

Jiri Vodnansky

Priority date (The priority date 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 date listed.)

1986-06-24

Filing date

1986-06-24

Publication date

1988-07-15

1986-06-24 Application filed by Otto Wichterle, Jiri Vacik, Jiri Michalek, Zuzana Krcova, Jiri Vodnansky filed Critical Otto Wichterle

1986-06-24 Priority to CS864639A priority Critical patent/CS257979B1/cs

1987-06-15 Priority to GB8713892A priority patent/GB2196973B/en

1987-06-22 Priority to IT20985/87A priority patent/IT1205164B/it

1987-06-23 Priority to FR878708811A priority patent/FR2600658B1/fr

1987-06-23 Priority to JP62154577A priority patent/JPS6322811A/ja

1987-06-23 Priority to CA000540374A priority patent/CA1293586C/en

1987-06-24 Priority to DE3720884A priority patent/DE3720884C2/de

1988-07-15 Publication of CS257979B1 publication Critical patent/CS257979B1/cs

Links

229920001480 hydrophilic copolymer Polymers 0.000 title claims abstract description 11
238000000034 method Methods 0.000 title claims description 13
238000004519 manufacturing process Methods 0.000 title claims description 6
239000000203 mixture Substances 0.000 claims abstract description 147
239000000178 monomer Substances 0.000 claims abstract description 85
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims abstract description 64
OLQFXOWPTQTLDP-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCO OLQFXOWPTQTLDP-UHFFFAOYSA-N 0.000 claims abstract description 50
229920001577 copolymer Polymers 0.000 claims abstract description 14
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 10
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 10
229910052700 potassium Inorganic materials 0.000 claims abstract description 9
229910052708 sodium Inorganic materials 0.000 claims abstract description 9
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 8
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 abstract description 8
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 8
239000011734 sodium Substances 0.000 claims abstract description 8
239000003999 initiator Substances 0.000 claims abstract description 7
239000011591 potassium Substances 0.000 claims abstract description 7
150000003863 ammonium salts Chemical class 0.000 claims abstract description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 108
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 85
235000011187 glycerol Nutrition 0.000 claims description 54
239000002904 solvent Substances 0.000 claims description 9
239000002798 polar solvent Substances 0.000 claims description 8
239000004971 Cross linker Substances 0.000 claims description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Substances [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
238000007334 copolymerization reaction Methods 0.000 claims description 6
239000012153 distilled water Substances 0.000 claims description 6
230000001476 alcoholic effect Effects 0.000 claims description 5
238000001035 drying Methods 0.000 claims description 5
150000003254 radicals Chemical class 0.000 claims description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
-1 2- (2-hydroxyethoxy) ethyl Chemical group 0.000 claims description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
230000009477 glass transition Effects 0.000 claims description 3
NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 claims description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
239000000908 ammonium hydroxide Substances 0.000 claims description 2
230000001143 conditioned effect Effects 0.000 claims description 2
239000000470 constituent Substances 0.000 claims description 2
150000002334 glycols Chemical class 0.000 claims description 2
230000000977 initiatory effect Effects 0.000 claims description 2
150000002978 peroxides Chemical class 0.000 claims description 2
JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims 1
239000011593 sulfur Substances 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
239000003431 cross linking reagent Substances 0.000 abstract description 2
239000000463 material Substances 0.000 description 69
230000008961 swelling Effects 0.000 description 69
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 66
DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 65
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 58
230000005855 radiation Effects 0.000 description 48
KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 43
RGBXDEHYFWDBKD-UHFFFAOYSA-N propan-2-yl propan-2-yloxy carbonate Chemical compound CC(C)OOC(=O)OC(C)C RGBXDEHYFWDBKD-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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 4
238000006116 polymerization reaction Methods 0.000 description 4
LLLCSBYSPJHDJX-UHFFFAOYSA-M potassium;2-methylprop-2-enoate Chemical compound [K+].CC(=C)C([O-])=O LLLCSBYSPJHDJX-UHFFFAOYSA-M 0.000 description 4
BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 3
230000003750 conditioning effect Effects 0.000 description 3
229960001760 dimethyl sulfoxide Drugs 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
239000004348 Glyceryl diacetate Substances 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
DZGUJOWBVDZNNF-UHFFFAOYSA-N azanium;2-methylprop-2-enoate Chemical compound [NH4+].CC(=C)C([O-])=O DZGUJOWBVDZNNF-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
IQIJRJNHZYUQSD-UHFFFAOYSA-N ethenyl(phenyl)diazene Chemical compound C=CN=NC1=CC=CC=C1 IQIJRJNHZYUQSD-UHFFFAOYSA-N 0.000 description 2
235000019443 glyceryl diacetate Nutrition 0.000 description 2
238000003754 machining Methods 0.000 description 2
ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 1
LQJPFRZLZSLIIO-UHFFFAOYSA-N 2,11-dimethyldodeca-2,10-dienediamide Chemical compound NC(=O)C(C)=CCCCCCCC=C(C)C(N)=O LQJPFRZLZSLIIO-UHFFFAOYSA-N 0.000 description 1
ARKDCHXUGNPHJU-UHFFFAOYSA-N 2,7-dimethylocta-2,6-dienediamide Chemical compound NC(=O)C(C)=CCCC=C(C)C(N)=O ARKDCHXUGNPHJU-UHFFFAOYSA-N 0.000 description 1
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 1
VAPQAGMSICPBKJ-UHFFFAOYSA-N 2-nitroacridine Chemical compound C1=CC=CC2=CC3=CC([N+](=O)[O-])=CC=C3N=C21 VAPQAGMSICPBKJ-UHFFFAOYSA-N 0.000 description 1
239000004160 Ammonium persulphate Substances 0.000 description 1
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
229910001870 ammonium persulfate Inorganic materials 0.000 description 1
235000019395 ammonium persulphate Nutrition 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000005266 casting Methods 0.000 description 1
238000009750 centrifugal casting Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
NVLHKSGUMYMKRR-UHFFFAOYSA-N dodeca-2,10-dienediamide Chemical compound NC(=O)C=CCCCCCCC=CC(N)=O NVLHKSGUMYMKRR-UHFFFAOYSA-N 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000011888 foil Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
229920000578 graft copolymer Polymers 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
229920001477 hydrophilic polymer Polymers 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
238000005498 polishing Methods 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229940047670 sodium acrylate Drugs 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 0.000 description 1
238000007614 solvation Methods 0.000 description 1
238000003786 synthesis reaction Methods 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

Landscapes

Physics & Mathematics (AREA)
General Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Materials For Medical Uses (AREA)
Eyeglasses (AREA)

CS864639A 1986-06-24 1986-06-24 Hydrophilic copolymer and method of its production CS257979B1 (en)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
CS864639A CS257979B1 (en)	1986-06-24	1986-06-24	Hydrophilic copolymer and method of its production
GB8713892A GB2196973B (en)	1986-06-24	1987-06-15	Hydrophilic copolymer and the method for producing thereof
IT20985/87A IT1205164B (it)	1986-06-24	1987-06-22	Copolimero idrofilo e metodo per la sua produzione
FR878708811A FR2600658B1 (fr)	1986-06-24	1987-06-23	Copolymere hydrophile et son procede de fabrication
JP62154577A JPS6322811A (ja)	1986-06-24	1987-06-23	親水性コポリマ−及びその製造方法
CA000540374A CA1293586C (en)	1986-06-24	1987-06-23	Hydrophilic copolymer and a method for its production
DE3720884A DE3720884C2 (de)	1986-06-24	1987-06-24	Hydrophiles Copolymer, Verfahren zu seiner Herstellung und seine Verwendung

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CS864639A CS257979B1 (en)	1986-06-24	1986-06-24	Hydrophilic copolymer and method of its production

Publications (1)

Publication Number	Publication Date
CS257979B1 true CS257979B1 (en)	1988-07-15

Family

ID=5389619

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS864639A CS257979B1 (en)	1986-06-24	1986-06-24	Hydrophilic copolymer and method of its production

Country Status (7)

Country	Link
JP (1)	JPS6322811A (it)
CA (1)	CA1293586C (it)
CS (1)	CS257979B1 (it)
DE (1)	DE3720884C2 (it)
FR (1)	FR2600658B1 (it)
GB (1)	GB2196973B (it)
IT (1)	IT1205164B (it)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
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
JPH0660042B2 (ja) *	1989-04-24	1994-08-10	株式会社エヌエムビー	セメント組成物の流動性低下防止剤およびセメント添加剤
US5641829A (en) *	1991-12-30	1997-06-24	Ppg Industries, Inc.	Coating compositions prepared from base neutralized, stable aqueous dispersion of hydroxyl functional acrylic polymers
US5342878A (en) *	1991-12-30	1994-08-30	Ppg Industries, Inc.	Base neutralized, stable, aqueous dispersion of a hydroxyl functional acrylic polymer and coating compositions prepared therefrom
US5464897A (en) *	1991-12-30	1995-11-07	Ppg Industries, Inc.	Aqueous fluoropolymer dispersions
US6267784B1 (en)	1998-05-01	2001-07-31	Benz Research And Development Corporation	Intraocular lens and haptics made of a copolymer
US6096799A (en) *	1998-05-07	2000-08-01	Benz Research & Development Corporation	Contact lens of high water content and high water balance
US6686431B2 (en)	2000-11-01	2004-02-03	Avery Dennison Corporation	Optical coating having low refractive index
WO2006113290A1 (en)	2005-04-13	2006-10-26	Benz Research & Development Corporation	Polymers for intraocular lenses
US7750079B2 (en) *	2005-08-09	2010-07-06	Coopervision International Holding Company, Lp	Compositions and methods for producing silicone hydrogel contact lenses

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3985697A (en) *	1972-10-18	1976-10-12	Uroptics International Incorporated	Hydrophilic contact lens material
JPS52102748A (en) *	1976-02-25	1977-08-29	Hoya Lens Co Ltd	Method of manufacturing soft contact lens
GB1534607A (en) *	1976-08-12	1978-12-06	Tre Corp	Hydrophilic contact lens material
GB2036765B (en) *	1978-11-30	1983-01-19	Global Vision Ltd	Soft contact lenses
EP0032443B1 (en) *	1980-01-10	1985-06-05	CooperVision Inc.	Cross-linked polymers for contact lenses
PL134871B1 (en) *	1982-05-31	1985-09-30	Polska Akademia Nauk Zaklad	Method of obtaining a polymer for making soft contact lenses
CS252224B1 (en) *	1985-07-31	1987-08-13	Otto Wichterle	Hydrophilic copolymer suitable eapecially for contact lenses and medicinal utilization and method of its producion

1986
- 1986-06-24 CS CS864639A patent/CS257979B1/cs not_active IP Right Cessation
1987
- 1987-06-15 GB GB8713892A patent/GB2196973B/en not_active Expired - Lifetime
- 1987-06-22 IT IT20985/87A patent/IT1205164B/it active
- 1987-06-23 FR FR878708811A patent/FR2600658B1/fr not_active Expired - Lifetime
- 1987-06-23 JP JP62154577A patent/JPS6322811A/ja active Pending
- 1987-06-23 CA CA000540374A patent/CA1293586C/en not_active Expired - Lifetime
- 1987-06-24 DE DE3720884A patent/DE3720884C2/de not_active Expired - Fee Related

Also Published As

Publication number	Publication date
GB8713892D0 (en)	1987-07-22
FR2600658A1 (fr)	1987-12-31
IT8720985A0 (it)	1987-06-22
JPS6322811A (ja)	1988-01-30
FR2600658B1 (fr)	1993-01-08
GB2196973B (en)	1991-01-02
GB2196973A (en)	1988-05-11
IT1205164B (it)	1989-03-15
DE3720884C2 (de)	1998-03-12
DE3720884A1 (de)	1988-01-14
CA1293586C (en)	1991-12-24

Legal Events

Date	Code	Title	Description
2000-06-30	IF00	In force as of 2000-06-30 in czech republic
2001-08-15	MK4A	Patent expired	Effective date: 20010624

Publication	Publication Date	Title
US5298533A (en)	1994-03-29	Polymer compositions for contact lenses
Refojo et al.	1965	Hydrogels from 2‐hydroxyethyl methacrylate and propylene glycol monoacrylate
JPS6330820A (ja)	1988-02-09	透明なヒドロゲルコンタクトレンズ用ポリマ−物質および該物質から成る光学的に透明な親水性コンタクトレンズ
US4430458A (en)	1984-02-07	Hydrogel-forming polymeric materials
CS257979B1 (en)	1988-07-15	Hydrophilic copolymer and method of its production
EP0823643A1 (en)	1998-02-11	Soft contact lens with high moisture content and method for producing the same
GB2157300A (en)	1985-10-23	Hydrophilic three-dimensional polymers
US4956432A (en)	1990-09-11	Hydrophilic transparent crosslinked copolymer and the method for producing thereof
CA1267492A (en)	1990-04-03	Hydrophilic copolymer suitable above all for contact lenses and medical purposes and a method of its preparation
CA2391817A1 (en)	2001-02-08	Biomedical compositions
EP0017512B1 (en)	1984-11-14	Polymeric materials, process for preparing them and shaped articles and contact lenses formed from them
CA1293577C (en)	1991-12-24	Hydrophilic copolymer suitable for contact lenses and medical application and a method for producing thereof
US4916197A (en)	1990-04-10	Hydrophilic copolymer and the method for producing thereof
US20020061993A1 (en)	2002-05-23	Polymerizable compositions for producing transparent polymeric substrates, resulting transparent polymeric substrates and applications thereof in optics
CA1332774C (en)	1994-10-25	Hydrophilic copolymer and the method for producing thereof
CZ284063B6 (cs)	1998-08-12	Kontaktní a intraokulární čočky s absorbéry ultrafialového záření a způsob jejich výroby
GB1350474A (en)	1974-04-18	Articles of bulk polymerised acrylic copolymers
JPH06289331A (ja)	1994-10-18	含水性ソフトコンタクトレンズ
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