CA1267492A - Hydrophilic copolymer suitable above all for contact lenses and medical purposes and a method of its preparation - Google Patents

Hydrophilic copolymer suitable above all for contact lenses and medical purposes and a method of its preparation

Info

Publication number: CA1267492A
Authority: CA; Canada
Prior art keywords: mixture; glycol dimethacrylate; water; con; hema
Prior art date: 1985-07-31
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

Application number

CA000514998A

Other languages

English (en)

French (fr)

Inventor

Otto Wichterle

Zuzana Krcova

Jiri Michalek

Jiri Vacik

Jiri Vodnansky

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Czech Academy of Sciences CAS

Original Assignee

Czech Academy of Sciences CAS

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.)

1985-07-31

Filing date

1986-07-30

Publication date

1990-04-03

1986-07-30 Application filed by Czech Academy of Sciences CAS filed Critical Czech Academy of Sciences CAS

1990-04-03 Application granted granted Critical

1990-04-03 Publication of CA1267492A publication Critical patent/CA1267492A/en

Status Expired legal-status Critical Current

Links

229920001480 hydrophilic copolymer Polymers 0.000 title abstract description 6
238000000034 method Methods 0.000 title description 8
238000002360 preparation method Methods 0.000 title description 5
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 abstract description 62
239000000178 monomer Substances 0.000 abstract description 51
229920001577 copolymer Polymers 0.000 abstract description 18
238000007334 copolymerization reaction Methods 0.000 abstract description 6
239000003431 cross linking reagent Substances 0.000 abstract description 6
239000003999 initiator Substances 0.000 abstract description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 126
239000000203 mixture Substances 0.000 description 106
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 74
206010042674 Swelling Diseases 0.000 description 63
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
230000008961 swelling Effects 0.000 description 62
239000000463 material Substances 0.000 description 57
OLQFXOWPTQTLDP-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCO OLQFXOWPTQTLDP-UHFFFAOYSA-N 0.000 description 56
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 55
DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 53
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 36
230000005855 radiation Effects 0.000 description 35
MZGMQAMKOBOIDR-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCO MZGMQAMKOBOIDR-UHFFFAOYSA-N 0.000 description 13
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 13
238000004519 manufacturing process Methods 0.000 description 9
229940044192 2-hydroxyethyl methacrylate Drugs 0.000 description 8
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 7
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
238000006116 polymerization reaction Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000002798 polar solvent Substances 0.000 description 5
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
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
238000001035 drying Methods 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
150000005690 diesters Chemical class 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
-1 benzoin ethers Chemical class 0.000 description 2
238000005266 casting Methods 0.000 description 2
238000009750 centrifugal casting Methods 0.000 description 2
229920001971 elastomer Polymers 0.000 description 2
239000000806 elastomer Substances 0.000 description 2
239000012467 final product Substances 0.000 description 2
230000009477 glass transition Effects 0.000 description 2
239000000017 hydrogel Substances 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
229940063557 methacrylate Drugs 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
229920006395 saturated elastomer Polymers 0.000 description 2
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
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-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
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
HTWRFCRQSLVESJ-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCOC(=O)C(C)=C HTWRFCRQSLVESJ-UHFFFAOYSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
102000015764 Eye Proteins Human genes 0.000 description 1
108010024515 Eye Proteins Proteins 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
125000000217 alkyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
AJTFTYHGFWNENF-UHFFFAOYSA-N azanium;hydroxy sulfate Chemical compound [NH4+].OOS([O-])(=O)=O AJTFTYHGFWNENF-UHFFFAOYSA-N 0.000 description 1
229960002130 benzoin Drugs 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
150000001470 diamides 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
150000002148 esters Chemical class 0.000 description 1
IQIJRJNHZYUQSD-UHFFFAOYSA-N ethenyl(phenyl)diazene Chemical compound C=CN=NC1=CC=CC=C1 IQIJRJNHZYUQSD-UHFFFAOYSA-N 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
206010016256 fatigue Diseases 0.000 description 1
239000011888 foil Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
235000019382 gum benzoic Nutrition 0.000 description 1
229920001477 hydrophilic polymer Polymers 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000001965 increasing effect Effects 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
230000007774 longterm Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
238000005498 polishing Methods 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920001897 terpolymer Polymers 0.000 description 1
229920006029 tetra-polymer Polymers 0.000 description 1
150000005691 triesters Chemical class 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 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
- 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)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Eyeglasses (AREA)
Materials For Medical Uses (AREA)

CA000514998A 1985-07-31 1986-07-30 Hydrophilic copolymer suitable above all for contact lenses and medical purposes and a method of its preparation Expired CA1267492A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CSPV5585-85		1985-07-31
CS855585A CS252224B1 (en)	1985-07-31	1985-07-31	Hydrophilic copolymer suitable eapecially for contact lenses and medicinal utilization and method of its producion

Publications (1)

Publication Number	Publication Date
CA1267492A true CA1267492A (en)	1990-04-03

Family

ID=5401021

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000514998A Expired CA1267492A (en)	1985-07-31	1986-07-30	Hydrophilic copolymer suitable above all for contact lenses and medical purposes and a method of its preparation

Country Status (7)

Country	Link
JP (1)	JPS6254709A (cs)
CA (1)	CA1267492A (cs)
CS (1)	CS252224B1 (cs)
DE (1)	DE3625869C2 (cs)
FR (1)	FR2585710B1 (cs)
GB (1)	GB2178435B (cs)
IT (1)	IT1213463B (cs)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CS256437B1 (en) *	1985-09-04	1988-04-15	Otto Wichterle	Hydrophilic copolymer especially for contact lenses and medicinal application and method of its production
CS257979B1 (en) *	1986-06-24	1988-07-15	Otto Wichterle	Hydrophilic copolymer and method of its production
US4871785A (en) *	1986-08-13	1989-10-03	Michael Froix	Clouding-resistant contact lens compositions
US5256751A (en) *	1993-02-08	1993-10-26	Vistakon, Inc.	Ophthalmic lens polymer incorporating acyclic monomer
AU2966595A (en) *	1994-07-26	1996-02-22	Bausch & Lomb Incorporated	Method of polymerizing methacrylate-based compositions
AU2015201371A1 (en) *	2014-03-31	2015-10-15	Johnson & Johnson Vision Care, Inc.	Silicone acrylamide copolymer

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB814009A (en) *	1956-04-24	1959-05-27	Otto Wichterle	Three-dimensional hydrophilic high polymeric articles
US3220960A (en) *	1960-12-21	1965-11-30	Wichterle Otto	Cross-linked hydrophilic polymers and articles made therefrom
DE1495381B2 (de) *	1963-09-07	1971-06-24	Czeskoslovenska akademie ved , Prag	Verfahren zur herstellung von kontaktlinsen oder kontakt linsenrohlingen aus quellfaehigen hydrogelen
DE2020329C3 (de) *	1969-05-13	1974-07-25	Ceskoslovenska Akademie Ved, Prag	Verfahren zur Herstellung spärlich vernetzter, glasklarer, quellfähiger, nicht formbeständiger Hydrogele
US3839304A (en) *	1973-02-12	1974-10-01	American Optical Corp	Soft contact lens and method of production thereof
DE2364856C3 (de) *	1973-12-28	1980-10-02	Teroson Gmbh, 6900 Heidelberg	Feuchtigkeitshärtende, lösungsmittelfreie Dichtungsmasse auf Basis von Organopolysiloxanen und Silikonöl
US4038264A (en) *	1974-01-07	1977-07-26	National Patent Development Corporation	Hema copolymers having high oxygen permeability
JPS543738B2 (cs) *	1974-05-27	1979-02-26

1985
- 1985-07-31 CS CS855585A patent/CS252224B1/cs not_active IP Right Cessation
1986
- 1986-07-16 GB GB8617318A patent/GB2178435B/en not_active Expired
- 1986-07-25 IT IT8621262A patent/IT1213463B/it active
- 1986-07-30 CA CA000514998A patent/CA1267492A/en not_active Expired
- 1986-07-30 FR FR868611033A patent/FR2585710B1/fr not_active Expired - Lifetime
- 1986-07-31 JP JP61178976A patent/JPS6254709A/ja active Pending
- 1986-07-31 DE DE3625869A patent/DE3625869C2/de not_active Expired - Fee Related

Also Published As

Publication number	Publication date
IT8621262A0 (it)	1986-07-25
DE3625869A1 (de)	1987-02-05
DE3625869C2 (de)	1994-08-04
FR2585710B1 (fr)	1990-08-03
CS558585A1 (en)	1987-01-15
IT1213463B (it)	1989-12-20
FR2585710A1 (fr)	1987-02-06
GB2178435B (en)	1989-12-13
GB2178435A (en)	1987-02-11
JPS6254709A (ja)	1987-03-10
GB8617318D0 (en)	1986-08-20
CS252224B1 (en)	1987-08-13

Legal Events

Date	Code	Title	Description
2003-04-03	MKLA	Lapsed

Publication	Publication Date	Title
US4130706A (en)	1978-12-19	Hydrophilic, oxygen permeable contact lens
US4430458A (en)	1984-02-07	Hydrogel-forming polymeric materials
WO2015161199A1 (en)	2015-10-22	(meth)acrylamide polymers for contact lens and intraocular lens
KR20190035353A (ko)	2019-04-03	안구질환 치료용 콘택트 렌즈 및 그 제조 방법
EP2203490A1 (en)	2010-07-07	Hydrogel with high water content and stability
JPH0117126B2 (cs)	1989-03-29
EP0129840B1 (en)	1988-12-28	Method of manufacturing shaped article of hydrogel
EP0228193A1 (en)	1987-07-08	Non-hydrous soft contact lens and process for producing the same
US4775731A (en)	1988-10-04	Hydrophilic three dimensional polymer and a method for production thereof
CA1293586C (en)	1991-12-24	Hydrophilic copolymer and a method for its production
GB2178435A (en)	1987-02-11	Hydrophilic copolymer suitable for contact lenses and medical purposes
US4882403A (en)	1989-11-21	Non-hydrous soft contact lens and process for producing the same
Muratore et al.	1999	Self-reinforcing hydrogels comprised of hydrophobic methyl methacrylate macromers copolymerised with either N-vinyl-2-pyrrolidone or 2-hydroxyethyl acrylate
US4956432A (en)	1990-09-11	Hydrophilic transparent crosslinked copolymer and the method for producing thereof
US4829126A (en)	1989-05-09	High water-absorptive soft contact lens
US4916197A (en)	1990-04-10	Hydrophilic copolymer and the method for producing thereof
CA1293577C (en)	1991-12-24	Hydrophilic copolymer suitable for contact lenses and medical application and a method for producing thereof
JPH11305172A (ja)	1999-11-05	含水性ソフトコンタクトレンズ
CA1332774C (en)	1994-10-25	Hydrophilic copolymer and the method for producing thereof
JPS5443284A (en)	1979-04-05	Dope for forming soft contact lens
JPH06289331A (ja)	1994-10-18	含水性ソフトコンタクトレンズ
JPH06123862A (ja)	1994-05-06	ソフトコンタクトレンズ
JPS6125734B2 (cs)	1986-06-17
KR910008260B1 (ko)	1991-10-12	고함수율 중합체의 제조방법
JPS6326617A (ja)	1988-02-04	含水性コンタクトレンズ