CA1060131A - Produits hydrophiles a base de copolymeres de type acrylate pour dispositifs phosthetiques composites - Google Patents

Produits hydrophiles a base de copolymeres de type acrylate pour dispositifs phosthetiques composites

Info

Publication number: CA1060131A
Authority: CA; Canada
Prior art keywords: methacrylate; weight; lens; vinyl; hydrophilic
Prior art date: 1972-12-06
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

CA293,431A

Other languages

English (en)

Inventor

Charles E. Erickson

Amar N. Neogi

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.)

Iolab Corp

Original Assignee

Precision Cosmet Co Inc

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.)

1972-12-06

Filing date

1977-12-20

Publication date

1979-08-07

1972-12-06 Priority claimed from CA158,175A external-priority patent/CA1027399A/fr

1977-12-20 Application filed by Precision Cosmet Co Inc filed Critical Precision Cosmet Co Inc

1977-12-20 Priority to CA293,431A priority Critical patent/CA1060131A/fr

1979-08-07 Application granted granted Critical

1979-08-07 Publication of CA1060131A publication Critical patent/CA1060131A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 35
229920001577 copolymer Polymers 0.000 title claims abstract description 11
239000002131 composite material Substances 0.000 title description 11
-1 hydroxyalkyl acrylate Chemical compound 0.000 claims abstract description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims abstract description 14
239000003054 catalyst Substances 0.000 claims abstract description 13
239000000126 substance Substances 0.000 claims abstract description 9
239000003431 cross linking reagent Substances 0.000 claims abstract description 8
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
229920001480 hydrophilic copolymer Polymers 0.000 claims abstract 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 19
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical group CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 16
YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical group COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 claims description 14
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 13
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 12
SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical group C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 8
229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 7
239000000463 material Substances 0.000 description 23
230000036571 hydration Effects 0.000 description 19
238000006703 hydration reaction Methods 0.000 description 19
239000000178 monomer Substances 0.000 description 12
230000002093 peripheral effect Effects 0.000 description 12
229920002554 vinyl polymer Polymers 0.000 description 12
OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 9
229920000642 polymer Polymers 0.000 description 8
229920001477 hydrophilic polymer Polymers 0.000 description 6
239000011159 matrix material Substances 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
229920003023 plastic Polymers 0.000 description 5
239000004033 plastic Substances 0.000 description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
238000004132 cross linking Methods 0.000 description 4
210000001508 eye Anatomy 0.000 description 4
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000000017 hydrogel Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
229920001451 polypropylene glycol Polymers 0.000 description 3
RTLULCVBFCRQKI-UHFFFAOYSA-N 1-amino-4-[3-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-4-sulfoanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S(O)(=O)=O)C=C1NC(C=1)=CC=C(S(O)(=O)=O)C=1NC1=NC(Cl)=NC(Cl)=N1 RTLULCVBFCRQKI-UHFFFAOYSA-N 0.000 description 2
DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
150000001252 acrylic acid derivatives Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
210000005252 bulbus oculi Anatomy 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
210000004087 cornea Anatomy 0.000 description 2
230000002526 effect on cardiovascular system Effects 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
150000002170 ethers Chemical class 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
239000012530 fluid Substances 0.000 description 2
150000002334 glycols Chemical class 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000002861 polymer material Substances 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
239000000985 reactive dye Substances 0.000 description 2
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-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
OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-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
XXVUSJBWYAWVQV-UHFFFAOYSA-N 1-ethenylpiperidine-2,6-dione Chemical compound C=CN1C(=O)CCCC1=O XXVUSJBWYAWVQV-UHFFFAOYSA-N 0.000 description 1
VOCDJQSAMZARGX-UHFFFAOYSA-N 1-ethenylpyrrolidine-2,5-dione Chemical compound C=CN1C(=O)CCC1=O VOCDJQSAMZARGX-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 description 1
ZMALNMQOXQXZRO-UHFFFAOYSA-N 4-ethenylmorpholin-3-one Chemical compound C=CN1CCOCC1=O ZMALNMQOXQXZRO-UHFFFAOYSA-N 0.000 description 1
CFZDMXAOSDDDRT-UHFFFAOYSA-N 4-ethenylmorpholine Chemical compound C=CN1CCOCC1 CFZDMXAOSDDDRT-UHFFFAOYSA-N 0.000 description 1
NNWNNQTUZYVQRK-UHFFFAOYSA-N 5-bromo-1h-pyrrolo[2,3-c]pyridine-2-carboxylic acid Chemical compound BrC1=NC=C2NC(C(=O)O)=CC2=C1 NNWNNQTUZYVQRK-UHFFFAOYSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
206010001557 Albinism Diseases 0.000 description 1
241000606643 Anaplasma centrale Species 0.000 description 1
206010003694 Atrophy Diseases 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
229920002574 CR-39 Polymers 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
101100285518 Drosophila melanogaster how gene Proteins 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
125000003047 N-acetyl group Chemical group 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920002873 Polyethylenimine Polymers 0.000 description 1
240000001987 Pyrus communis Species 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
238000005299 abrasion Methods 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000005250 alkyl acrylate group Chemical group 0.000 description 1
210000002159 anterior chamber Anatomy 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
238000010420 art technique Methods 0.000 description 1
230000037444 atrophy Effects 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
125000004386 diacrylate group Chemical group 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
210000000981 epithelium Anatomy 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
AFIQVBFAKUPHOA-UHFFFAOYSA-N ethenyl 2-methoxyacetate Chemical compound COCC(=O)OC=C AFIQVBFAKUPHOA-UHFFFAOYSA-N 0.000 description 1
BLCTWBJQROOONQ-UHFFFAOYSA-N ethenyl prop-2-enoate Chemical compound C=COC(=O)C=C BLCTWBJQROOONQ-UHFFFAOYSA-N 0.000 description 1
125000005822 ethenylethoxy group Chemical group [H]\[#6]([H])=[#6](\[H])C([H])([H])C([H])([H])[#8]-* 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
229940093476 ethylene glycol Drugs 0.000 description 1
239000000835 fiber Substances 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
230000005660 hydrophilic surface Effects 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
239000007943 implant Substances 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
150000005209 naphthoic acids Chemical class 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
238000006748 scratching Methods 0.000 description 1
230000002393 scratching effect Effects 0.000 description 1
239000000344 soap Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000004901 spalling Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Landscapes

Eyeglasses (AREA)
Materials For Medical Uses (AREA)

CA293,431A 1972-12-06 1977-12-20 Produits hydrophiles a base de copolymeres de type acrylate pour dispositifs phosthetiques composites Expired CA1060131A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA293,431A CA1060131A (fr)	1972-12-06	1977-12-20	Produits hydrophiles a base de copolymeres de type acrylate pour dispositifs phosthetiques composites

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CA158,175A CA1027399A (fr)	1972-12-06	1972-12-06	Protheses composees a base de polymeres
CA293,431A CA1060131A (fr)	1972-12-06	1977-12-20	Produits hydrophiles a base de copolymeres de type acrylate pour dispositifs phosthetiques composites

Publications (1)

Publication Number	Publication Date
CA1060131A true CA1060131A (fr)	1979-08-07

Family

ID=25667167

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA293,431A Expired CA1060131A (fr)	1972-12-06	1977-12-20	Produits hydrophiles a base de copolymeres de type acrylate pour dispositifs phosthetiques composites

Country Status (1)

Country	Link
CA (1)	CA1060131A (fr)

1977
- 1977-12-20 CA CA293,431A patent/CA1060131A/fr not_active Expired

Publication	Publication Date	Title
US3876581A (en)	1975-04-08	Hydrophilic polymer composition for prosthetic devices
US4121885A (en)	1978-10-24	Method to produce a composite contact lens
US4093361A (en)	1978-06-06	Composite prosthetic polymeric devices
EP1096905B1 (fr)	2006-02-08	Lentilles arretant les rayonnements ultraviolets et materiau contenant des benzotriazoles et des benzophenones
US4619793A (en)	1986-10-28	Method of producing annealed polyvinyl alcohol contact lens
US8662663B2 (en)	2014-03-04	Hybrid soft contact lens, and production method and hydration treatment method thereof
EP1286823B1 (fr)	2009-06-17	Lentilles ophtalmiques et compositions, ainsi que production de celles-ci
EP1083844B1 (fr)	2004-06-16	Cristallin artificiel
US7588334B2 (en)	2009-09-15	Contact lens
CA1242299A (fr)	1988-09-20	Polymeres hydrophiles, et verres de contact qui en sont faits
US4866148A (en)	1989-09-12	Hydrophilic copolymers, the use thereof as biomedical materials and contact-optical articles produced therefrom
US8247511B2 (en)	2012-08-21	Water plasticized high refractive index polymer for ophthalmic applications
EP2240804A2 (fr)	2010-10-20	Préparations polymérisables pour lentilles de contact et lentilles de contact ainsi obtenues
US5135965A (en)	1992-08-04	Hydrogel-forming polymers used in intraocular lenses
CA1251069A (fr)	1989-03-14	Lentille corneennes hydrophiles pouvant etre portees pendant une longue periode
CA1193795A (fr)	1985-09-17	Articles biomedicaux a base de copolymeres a faible teneur en n-vinyl lactam
US3803093A (en)	1974-04-09	Methyl methacrylate copolymer which may be hydrated
EP0188110A1 (fr)	1986-07-23	Polymères formant des hydrogels
KR100286971B1 (ko)	2001-04-16	안용 렌즈 재료 및 이의 제조방법
US4640965A (en)	1987-02-03	Hydrogel compositions using p-(2-hydroxyhexafluoroisopropyl) styrene as a comonomer
US4745158A (en)	1988-05-17	Highly water-absorptive optical material
CA1260193A (fr)	1989-09-26	Object doux de contact optique
JPH0624584B2 (ja)	1994-04-06	光学的人口器官及びその製造法
US8408697B2 (en)	2013-04-02	High refractive index oxygen permeable contact lens system and method
CA1260196A (fr)	1989-09-26	Article doux de contact optique faiblement hydrophile