CS270345B1 - Hydrophilic transparent cross-linked copolymer and method of its production - Google Patents

Hydrophilic transparent cross-linked copolymer and method of its production Download PDF

Info

Publication number: CS270345B1
Authority: CS; Czechoslovakia
Prior art keywords: weight; formula; monomers; copolymerization; och
Prior art date: 1988-06-08

Application number

CS883974A

Other languages

Czech (cs)

English (en)

Other versions

CS397488A1 (en

Inventor

Jiri Ing Csc Vacik

Blahoslav Ing Csc Obereigner

Dana Ing Souckova

Original Assignee

Vacik Jiri

Blahoslav Ing Csc Obereigner

Dana Ing Souckova

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.)

1988-06-08

Filing date

1988-06-08

Publication date

1990-06-13

1988-06-08 Application filed by Vacik Jiri, Blahoslav Ing Csc Obereigner, Dana Ing Souckova filed Critical Vacik Jiri

1988-06-08 Priority to CS883974A priority Critical patent/CS270345B1/cs

1989-06-07 Priority to JP1143191A priority patent/JPH0243208A/ja

1989-06-07 Priority to US07/362,763 priority patent/US4956432A/en

1989-06-08 Priority to EP89110417A priority patent/EP0345794A3/en

1989-11-14 Publication of CS397488A1 publication Critical patent/CS397488A1/cs

1990-06-13 Publication of CS270345B1 publication Critical patent/CS270345B1/cs

Links

229920001577 copolymer Polymers 0.000 title claims abstract description 13
238000000034 method Methods 0.000 title claims abstract description 11
238000004519 manufacturing process Methods 0.000 title claims abstract description 8
239000000178 monomer Substances 0.000 claims abstract description 37
238000007334 copolymerization reaction Methods 0.000 claims abstract description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
229920001480 hydrophilic copolymer Polymers 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
239000003999 initiator Substances 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
239000003431 cross linking reagent Substances 0.000 claims abstract 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 77
239000000203 mixture Substances 0.000 claims description 53
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
239000002798 polar solvent Substances 0.000 claims description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
-1 benzoin ethers Chemical class 0.000 claims description 4
238000005266 casting Methods 0.000 claims description 4
238000009750 centrifugal casting Methods 0.000 claims description 4
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
239000004342 Benzoyl peroxide Substances 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 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
150000002334 glycols Chemical class 0.000 claims description 2
150000002978 peroxides Chemical class 0.000 claims description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
239000004971 Cross linker Substances 0.000 claims 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
244000028419 Styrax benzoin Species 0.000 claims 1
235000000126 Styrax benzoin Nutrition 0.000 claims 1
235000008411 Sumatra benzointree Nutrition 0.000 claims 1
229960002130 benzoin Drugs 0.000 claims 1
239000007844 bleaching agent Substances 0.000 claims 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 claims 1
235000019382 gum benzoic Nutrition 0.000 claims 1
238000010526 radical polymerization reaction Methods 0.000 claims 1
239000012966 redox initiator Substances 0.000 claims 1
229920000642 polymer Polymers 0.000 abstract description 8
125000000217 alkyl group Chemical group 0.000 abstract 1
229920001519 homopolymer Polymers 0.000 abstract 1
239000000499 gel Substances 0.000 description 62
101000663001 Mus musculus TNFAIP3-interacting protein 1 Proteins 0.000 description 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000463 material Substances 0.000 description 8
UJKWLAZYSLJTKA-UHFFFAOYSA-N edma Chemical compound O1CCOC2=CC(CC(C)NC)=CC=C21 UJKWLAZYSLJTKA-UHFFFAOYSA-N 0.000 description 5
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 4
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
230000008961 swelling Effects 0.000 description 4
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
241000183024 Populus tremula Species 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
QAXCWBIVFCEYGG-UHFFFAOYSA-N 1-methylquinazolin-4-one Chemical compound C1=CC=C2N(C)C=NC(=O)C2=C1 QAXCWBIVFCEYGG-UHFFFAOYSA-N 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 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
230000035699 permeability Effects 0.000 description 2
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 2
235000013580 sausages Nutrition 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
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 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
UVRCNEIYXSRHNT-UHFFFAOYSA-N 3-ethylpent-2-enamide Chemical compound CCC(CC)=CC(N)=O UVRCNEIYXSRHNT-UHFFFAOYSA-N 0.000 description 1
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
241000282994 Cervidae Species 0.000 description 1
239000004348 Glyceryl diacetate Substances 0.000 description 1
PSERPAMCPRGQBZ-UHFFFAOYSA-N OS(O)=O.OS(=O)S(O)(=O)=O Chemical compound OS(O)=O.OS(=O)S(O)(=O)=O PSERPAMCPRGQBZ-UHFFFAOYSA-N 0.000 description 1
206010047700 Vomiting Diseases 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
239000011324 bead Substances 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
230000009477 glass transition Effects 0.000 description 1
235000019443 glyceryl diacetate Nutrition 0.000 description 1
239000000017 hydrogel Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000003754 machining Methods 0.000 description 1
229920002521 macromolecule Polymers 0.000 description 1
125000005395 methacrylic acid group Chemical group 0.000 description 1
238000000465 moulding Methods 0.000 description 1
OKPYIWASQZGASP-UHFFFAOYSA-N n-(2-hydroxypropyl)-2-methylprop-2-enamide Chemical compound CC(O)CNC(=O)C(C)=C OKPYIWASQZGASP-UHFFFAOYSA-N 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
238000005191 phase separation Methods 0.000 description 1
229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical class OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
238000010025 steaming Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
PCYCVCFVEKMHGA-UHFFFAOYSA-N thiirane 1-oxide Chemical compound O=S1CC1 PCYCVCFVEKMHGA-UHFFFAOYSA-N 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
238000005406 washing 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
- C08F20/00—Homopolymers and 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F20/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
- 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

Physics & Mathematics (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Health & Medical Sciences (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Eyeglasses (AREA)
Polymerisation Methods In General (AREA)
Polymerization Catalysts (AREA)

CS883974A 1988-06-08 1988-06-08 Hydrophilic transparent cross-linked copolymer and method of its production CS270345B1 (en)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
CS883974A CS270345B1 (en)	1988-06-08	1988-06-08	Hydrophilic transparent cross-linked copolymer and method of its production
JP1143191A JPH0243208A (ja)	1988-06-08	1989-06-07	透明な親水性架橋コポリマー及びその製造方法
US07/362,763 US4956432A (en)	1988-06-08	1989-06-07	Hydrophilic transparent crosslinked copolymer and the method for producing thereof
EP89110417A EP0345794A3 (en)	1988-06-08	1989-06-08	Hydrophilic transparent crosslinked copolymers and method for their preparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CS883974A CS270345B1 (en)	1988-06-08	1988-06-08	Hydrophilic transparent cross-linked copolymer and method of its production

Publications (2)

Publication Number	Publication Date
CS397488A1 CS397488A1 (en)	1989-11-14
CS270345B1 true CS270345B1 (en)	1990-06-13

Family

ID=5381367

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS883974A CS270345B1 (en)	1988-06-08	1988-06-08	Hydrophilic transparent cross-linked copolymer and method of its production

Country Status (4)

Country	Link
US (1)	US4956432A (ja)
EP (1)	EP0345794A3 (ja)
JP (1)	JPH0243208A (ja)
CS (1)	CS270345B1 (ja)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5286450A (en) *	1992-06-01	1994-02-15	Eastman Kodak Company	Bilirubin assay using crosslinkable polymers
US5480950A (en) *	1992-09-28	1996-01-02	Kabi Pharmacia Ophthalmics, Inc.	High refractive index hydrogels and uses thereof
US6132462A (en) *	1995-12-22	2000-10-17	Santen Pharmaceutical Co., Ltd.	Copolymers formed from three components and intraocular lenses made thereof
CN1089754C (zh)	1997-06-05	2002-08-28	参天制药株式会社	用作聚合物成分的衣康酸衍生物
CN1213671A (zh)	1997-10-07	1999-04-14	参天制药株式会社	四成分共聚物及由该共聚物形成的眼用透镜
KR20010016207A (ko) *	2000-11-22	2001-03-05	김쌍기	콘택트 렌즈의 재료 및 구조
EP2781939B1 (en)	2013-03-18	2015-11-04	poLight AS	Deformable polymeric lens

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA993877A (en) *	1972-01-14	1976-07-27	David I. Randall	N-(1-(2-pyrrolidonyl)ethyl) acrylamide and polymers thereof

1988
- 1988-06-08 CS CS883974A patent/CS270345B1/cs not_active IP Right Cessation
1989
- 1989-06-07 JP JP1143191A patent/JPH0243208A/ja active Pending
- 1989-06-07 US US07/362,763 patent/US4956432A/en not_active Expired - Fee Related
- 1989-06-08 EP EP89110417A patent/EP0345794A3/en not_active Withdrawn

Also Published As

Publication number	Publication date
JPH0243208A (ja)	1990-02-13
US4956432A (en)	1990-09-11
EP0345794A2 (en)	1989-12-13
CS397488A1 (en)	1989-11-14
EP0345794A3 (en)	1990-08-22

Legal Events

Date	Code	Title	Description
2000-06-30	IF00	In force as of 2000-06-30 in czech republic
2002-03-13	MM4A	Patent lapsed due to non-payment of fee	Effective date: 20010608

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US20010044482A1 (en)	2001-11-22	Interpenetrating polymer network hydrophilic hydrogels for contact lens
US4279795A (en)	1981-07-21	Hydrophilic-hydrophobic graft copolymers for self-reinforcing hydrogels
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JP2021535447A (ja)	2021-12-16	眼科用デバイス
JPH0273812A (ja)	1990-03-13	親水性コポリマー及びその製造方法
KR20240150432A (ko)	2024-10-15	안과용 장치
JPS63234001A (ja)	1988-09-29	ソフトコンタクトレンズの製造方法
JPH0115847B2 (ja)	1989-03-20
JPS6125734B2 (ja)	1986-06-17
JPS63210116A (ja)	1988-08-31	コンタクトレンズ材料