CA1089611A - Fabrication de lentilles corneennes souples et compose utilise a cet effet - Google Patents

Fabrication de lentilles corneennes souples et compose utilise a cet effet

Info

Publication number: CA1089611A
Authority: CA; Canada
Prior art keywords: polymer; mold; film; tube; oxygen
Prior art date: 1974-11-21
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

CA315,466A

Other languages

English (en)

Inventor

Albert R. Le Boeuf

William R. Grovesteen

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.)

Warner Lambert Co LLC

Original Assignee

Warner Lambert Co LLC

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.)

1974-11-21

Filing date

1978-10-31

Publication date

1980-11-18

1974-11-21 Priority claimed from US05/526,022 external-priority patent/US3978164A/en

1978-10-31 Application filed by Warner Lambert Co LLC filed Critical Warner Lambert Co LLC

1978-10-31 Priority to CA315,466A priority Critical patent/CA1089611A/fr

1980-11-18 Application granted granted Critical

1980-11-18 Publication of CA1089611A publication Critical patent/CA1089611A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title description 74
238000004519 manufacturing process Methods 0.000 title description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 30
239000001301 oxygen Substances 0.000 claims abstract description 30
229910052760 oxygen Inorganic materials 0.000 claims abstract description 30
238000005266 casting Methods 0.000 claims abstract description 24
229920000642 polymer Polymers 0.000 claims abstract description 22
239000002250 absorbent Substances 0.000 claims abstract description 16
230000002745 absorbent Effects 0.000 claims abstract description 14
230000000379 polymerizing effect Effects 0.000 claims abstract description 9
UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 claims abstract description 6
238000006116 polymerization reaction Methods 0.000 claims description 58
229920006267 polyester film Polymers 0.000 claims description 17
239000007787 solid Substances 0.000 claims description 6
229920001730 Moisture cure polyurethane Polymers 0.000 claims description 5
-1 polytetrafluoroethylene Polymers 0.000 claims description 5
239000012530 fluid Substances 0.000 claims description 3
229920001343 polytetrafluoroethylene Polymers 0.000 claims description 3
239000004810 polytetrafluoroethylene Substances 0.000 claims description 3
239000005020 polyethylene terephthalate Substances 0.000 claims 1
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 45
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 35
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
238000000034 method Methods 0.000 description 17
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 16
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
230000036571 hydration Effects 0.000 description 12
238000006703 hydration reaction Methods 0.000 description 12
239000000463 material Substances 0.000 description 12
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
239000003814 drug Substances 0.000 description 11
239000003112 inhibitor Substances 0.000 description 10
239000003999 initiator Substances 0.000 description 9
239000000178 monomer Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
238000010438 heat treatment Methods 0.000 description 8
238000009472 formulation Methods 0.000 description 7
229920000728 polyester Polymers 0.000 description 7
239000003505 polymerization initiator Substances 0.000 description 7
238000005520 cutting process Methods 0.000 description 6
UJKWLAZYSLJTKA-UHFFFAOYSA-N edma Chemical compound O1CCOC2=CC(CC(C)NC)=CC=C21 UJKWLAZYSLJTKA-UHFFFAOYSA-N 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
229940063559 methacrylic acid Drugs 0.000 description 6
238000011109 contamination Methods 0.000 description 5
238000010559 graft polymerization reaction Methods 0.000 description 5
238000000465 moulding Methods 0.000 description 5
229920002799 BoPET Polymers 0.000 description 4
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
239000005041 Mylar™ Substances 0.000 description 4
239000007975 buffered saline Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
229960005419 nitrogen Drugs 0.000 description 4
239000007870 radical polymerization initiator Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000012632 extractable Substances 0.000 description 3
239000011521 glass Substances 0.000 description 3
230000000887 hydrating effect Effects 0.000 description 3
238000003780 insertion Methods 0.000 description 3
230000037431 insertion Effects 0.000 description 3
238000003754 machining Methods 0.000 description 3
238000005498 polishing Methods 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-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
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
230000002411 adverse Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000012662 bulk polymerization Methods 0.000 description 2
NSGQRLUGQNBHLD-UHFFFAOYSA-N butan-2-yl butan-2-yloxycarbonyloxy carbonate Chemical compound CCC(C)OC(=O)OOC(=O)OC(C)CC NSGQRLUGQNBHLD-UHFFFAOYSA-N 0.000 description 2
ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
238000011067 equilibration Methods 0.000 description 2
229920001480 hydrophilic copolymer Polymers 0.000 description 2
239000007943 implant Substances 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000002156 mixing Methods 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
239000002504 physiological saline solution Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000005096 rolling process Methods 0.000 description 2
238000007493 shaping process Methods 0.000 description 2
239000010959 steel Substances 0.000 description 2
QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 1
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
241001106067 Atropa Species 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
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 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
241000357437 Mola Species 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
QZVCTJOXCFMACW-UHFFFAOYSA-N Phenoxybenzamine Chemical compound C=1C=CC=CC=1CN(CCCl)C(C)COC1=CC=CC=C1 QZVCTJOXCFMACW-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
241000613437 Xema Species 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
230000002421 anti-septic effect Effects 0.000 description 1
229940064004 antiseptic throat preparations Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
201000009310 astigmatism Diseases 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
229960000910 bethanechol Drugs 0.000 description 1
NZUPCNDJBJXXRF-UHFFFAOYSA-O bethanechol Chemical compound C[N+](C)(C)CC(C)OC(N)=O NZUPCNDJBJXXRF-UHFFFAOYSA-O 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000008366 buffered solution Substances 0.000 description 1
229960004484 carbachol Drugs 0.000 description 1
AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
PBKVEOSEPXMKDN-LZHUFOCISA-N chembl2311030 Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)C)C(C)C)=C3C2=CNC3=C1.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)CC)C(C)C)=C3C2=CNC3=C1.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)CC(C)C)C(C)C)=C3C2=CNC3=C1.C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@H]1CN(C)[C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C(C)C)C1=CC=CC=C1 PBKVEOSEPXMKDN-LZHUFOCISA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
229960001334 corticosteroids Drugs 0.000 description 1
238000001723 curing Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
229940061607 dibasic sodium phosphate Drugs 0.000 description 1
229940087490 dibenzyline Drugs 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229920000578 graft copolymer Polymers 0.000 description 1
238000000227 grinding Methods 0.000 description 1
201000006318 hyperopia Diseases 0.000 description 1
230000004305 hyperopia Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
NZWOPGCLSHLLPA-UHFFFAOYSA-N methacholine Chemical compound C[N+](C)(C)CC(C)OC(C)=O NZWOPGCLSHLLPA-UHFFFAOYSA-N 0.000 description 1
229960002329 methacholine Drugs 0.000 description 1
229940045641 monobasic sodium phosphate Drugs 0.000 description 1
229910000403 monosodium phosphate Inorganic materials 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
208000001491 myopia Diseases 0.000 description 1
230000004379 myopia Effects 0.000 description 1
239000013618 particulate matter Substances 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
229960001416 pilocarpine Drugs 0.000 description 1
229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000003847 radiation curing Methods 0.000 description 1
238000010526 radical polymerization reaction Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000002791 soaking Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
235000011008 sodium phosphates Nutrition 0.000 description 1
238000007614 solvation Methods 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1

Landscapes

Casting Or Compression Moulding Of Plastics Or The Like (AREA)

CA315,466A 1974-11-21 1978-10-31 Fabrication de lentilles corneennes souples et compose utilise a cet effet Expired CA1089611A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA315,466A CA1089611A (fr)	1974-11-21	1978-10-31	Fabrication de lentilles corneennes souples et compose utilise a cet effet

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US05/526,022 US3978164A (en)	1974-11-21	1974-11-21	Pyrrolidone-methacrylate graft copolymers from 3-stage polymerization process
US526,022		1974-11-21
CA240,087A CA1076477A (fr)	1974-11-21	1975-11-20	Methode de fabrication d'une lentille souple et composition
CA315,466A CA1089611A (fr)	1974-11-21	1978-10-31	Fabrication de lentilles corneennes souples et compose utilise a cet effet

Publications (1)

Publication Number	Publication Date
CA1089611A true CA1089611A (fr)	1980-11-18

Family

ID=27164206

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA315,466A Expired CA1089611A (fr)	1974-11-21	1978-10-31	Fabrication de lentilles corneennes souples et compose utilise a cet effet

Country Status (1)

Country	Link
CA (1)	CA1089611A (fr)

1978
- 1978-10-31 CA CA315,466A patent/CA1089611A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-11-18	MKEX	Expiry

Publication	Publication Date	Title
US4018853A (en)	1977-04-19	Crosslinked, hydrophilic rods of pyrrolidone-methacrylate graft copolymers
US4045547A (en)	1977-08-30	Fabrication of soft contact lens and composition therefor
US3978164A (en)	1976-08-31	Pyrrolidone-methacrylate graft copolymers from 3-stage polymerization process
US4054624A (en)	1977-10-18	Preparing a hydrated contact lens
EP1623269B1 (fr)	2017-05-10	Lentilles de contact a base d'hydrogel, systemes d'emballage et procedes de production associes
US3983083A (en)	1976-09-28	Soft contact lenses and process for preparation thereof
US3700761A (en)	1972-10-24	Fabrication of soft plastic contact lens blank
US3660545A (en)	1972-05-02	Method of centrifugally casting thin edged corneal contact lenses
US5135965A (en)	1992-08-04	Hydrogel-forming polymers used in intraocular lenses
JPH10507418A (ja)	1998-07-21	プラスチック製の型部品の処理方法
GB1593660A (en)	1981-07-22	Water-swellable copolymers
JP2006508716A (ja)	2006-03-16	ポリ（オキシアルキレン）含有ポリマー材料の安定化
TW200813518A (en)	2008-03-16	Package mold combination
US3816571A (en)	1974-06-11	Fabrication of soft plastic lens
US3841985A (en)	1974-10-15	Irradiated composition for soft contact lens
CA1311095C (fr)	1992-12-08	Polymeres formant des hydrogels
US6030554A (en)	2000-02-29	Method of sterilizing intraocular lens by electron beam
GB1588745A (en)	1981-04-29	Cross-linked polymer composition for use in soft contact lenses
US4022204A (en)	1977-05-10	Dimensionally stable shaped eye bandages
CA1089611A (fr)	1980-11-18	Fabrication de lentilles corneennes souples et compose utilise a cet effet
US3829329A (en)	1974-08-13	Method of cleaning a soft hydrophilic contact lens
WO2005113028A1 (fr)	2005-12-01	Procédé pour extraire des dispositifs biomédicaux
EP3363862B1 (fr)	2020-11-11	Composition pour lentille de contact souple photochromique et son procédé de préparation
US3822196A (en)	1974-07-02	Fabrication of soft plastic contact lens blank and composition therefor
JPS6271924A (ja)	1987-04-02	軟質コンタクトレンズ素材の製造法