CA1167198A - Lens having a high refractive index with a low dispersion - Google Patents
Lens having a high refractive index with a low dispersionInfo
- Publication number
- CA1167198A CA1167198A CA000388393A CA388393A CA1167198A CA 1167198 A CA1167198 A CA 1167198A CA 000388393 A CA000388393 A CA 000388393A CA 388393 A CA388393 A CA 388393A CA 1167198 A CA1167198 A CA 1167198A
- Authority
- CA
- Canada
- Prior art keywords
- lens
- refractive index
- high refractive
- low dispersion
- monomer
- Prior art date
- 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
Links
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
-
- 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
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/301—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one oxygen in the alcohol moiety
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31645—Next to addition polymer from unsaturated monomers
- Y10T428/31649—Ester, halide or nitrile of addition polymer
Abstract
ABSTRACT OF THE DISCLOSURE
A lens having a high refractive index with a low dispersion produced by copolymerizing polyfunctional allyl monomer with at least one selected from the monomer group represented by the general formula A:
...... A
X : H, CH3, C?
Y: H, CH3, C2H5, n-C3H7, iso-C3H7- OCH3, C6H11' C?, Br, CH2C? CH2Br, C6H5, CH2C6H5' SCH3 m - 0, 1, 2 n - 0, 1, 2, 3, 4, 5.
This lens is excellent in its transmittance, pencil hardness, impact resistance, dyeability, coating adhesion, solvent resistance, workability, etc.
A lens having a high refractive index with a low dispersion produced by copolymerizing polyfunctional allyl monomer with at least one selected from the monomer group represented by the general formula A:
...... A
X : H, CH3, C?
Y: H, CH3, C2H5, n-C3H7, iso-C3H7- OCH3, C6H11' C?, Br, CH2C? CH2Br, C6H5, CH2C6H5' SCH3 m - 0, 1, 2 n - 0, 1, 2, 3, 4, 5.
This lens is excellent in its transmittance, pencil hardness, impact resistance, dyeability, coating adhesion, solvent resistance, workability, etc.
Description
7~
BACKGROUND OF THE INVFJNTION
1. Field of the Invention This invention relates to a plastic lens having a high refractive index with a low dispersion.
BACKGROUND OF THE INVFJNTION
1. Field of the Invention This invention relates to a plastic lens having a high refractive index with a low dispersion.
2. Description of the Prior Art Recently plastic lenses have been widely uscd instead of inorganic glass lenses, because plastic lenses are more advantageous than inorganic glass lenses in the many properties such as lightness, sa-fety, workability, dyeability, etc. For example, lenses made from diethylene glycol bisallyl carbonate (hereinafter referred to CR39~ have been widely used.
But, lenses made from ~R39 have such a disadvantage that the lenses must be thicker than inorganic glass lenses, because of their relatively low refractive index such as 1.499.
As the material for the plastic lenses with a high refractive index are known polystyrene or polycarbonate. However, they are considerably inferior to the polymer of CR39 in the superficial hardness, solvent resistance, wea~herability, cutting-ability, dyeability, etc. Moreover, they have such a large dispersion tha~ they are unfavorable as spectacle lens.
We ha~e now found that the copolymer produced from polyfunctional allyl monomer and ~meth~ acrylate having an aromatic ring enables to produce a plastic lens having a low dispersion and a high refractive index, so that ~ 6~7~
above-said drawbacks are dissolved.
An object of this invention is to provide a plastic lens having a high refractive index with a low dispersion.
SUMMARY OF THE INVENTION
This invention relates to a lens obtained by a process comprising polymerizing polyfunctional allyl monomer with at least one selected from the monomer group represented by the general formula A:
CHz = C - COO -~ CH2 ~ ~ / n .~................. A
X : H, CH3, CQ
But, lenses made from ~R39 have such a disadvantage that the lenses must be thicker than inorganic glass lenses, because of their relatively low refractive index such as 1.499.
As the material for the plastic lenses with a high refractive index are known polystyrene or polycarbonate. However, they are considerably inferior to the polymer of CR39 in the superficial hardness, solvent resistance, wea~herability, cutting-ability, dyeability, etc. Moreover, they have such a large dispersion tha~ they are unfavorable as spectacle lens.
We ha~e now found that the copolymer produced from polyfunctional allyl monomer and ~meth~ acrylate having an aromatic ring enables to produce a plastic lens having a low dispersion and a high refractive index, so that ~ 6~7~
above-said drawbacks are dissolved.
An object of this invention is to provide a plastic lens having a high refractive index with a low dispersion.
SUMMARY OF THE INVENTION
This invention relates to a lens obtained by a process comprising polymerizing polyfunctional allyl monomer with at least one selected from the monomer group represented by the general formula A:
CHz = C - COO -~ CH2 ~ ~ / n .~................. A
X : H, CH3, CQ
3' C2H5~ n-C3H7~ iso-c3H7~ OCH3, C~Hll, , ~ CH2CQ~ CHzBr, C6H5, CH2CGH5, SCH3 m = 0, 1, 2 n = 0, 1, 2, 3, 4, 5.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
As the polyfunctional allyl monomer of this invention are cited diallylorthophthalate, diallylisophth~late, diallylterephthalate, diallylchlorendate, triallylcyanurate, triallylisocyanurate 7 etc. They can be used 501ely or in ~3 ~7~
a mixture of two or more. In the mixture of diallyl monomer and triallyl monomer, triallyl monomer is preferably used in an amount of at mos~ 10 wt.%. The use of triallyl monomer in an amount more than 10 wt.~ is practically unfavorable, because of lowering the impact resistance of the lens obtained therefrom.
The lens of this in~ention can be prepared by the method comprising pouring the mixed solution consisting of above-said monomers and a polymerizatîon initiator into a mold mad0 of two plates of glass mold and a plastic gasket, and ~hen heating or irradiating with ultraviolet ray the resulting one.
The lens of this invention has an improved dispersion compared with well known lens made from polycarbonate or polystyrene, so that very l;ttle chromatic aberration appears in spite of the high refractive index in the lens 9 which is one of the features of this invention. The superficial hardness 3 solvent resistance, and workability thereof are considerably superior to those of polycarbonate lens or polystyrene lens. Coating glass film thereon by vacuum evaporation coating method can be easily effected, so that the ability of anti-reflectlon of the lens is excellent.
This invention will be more clearly understood with reference to the following Examples.
~ ~7~
Example 1 A mixed solution consisting of 30 wt. parts of phenyl methacrylate, 70 wt. parts of diallylisophthalate and 2.5 wt. parts of diisopropylperoxydicarbonate was poured into a mold made of two plates of glass mold, and a gasket of ethylene-vinylacetate copolymer, and the resulting one was heated to raise gradually the temperatur~ from 40C to 90C in 24 hours. After end of the polymerization, the lens was taken out of the mold, and then was post-cured at 120C
for one hour. The resulting lens had 1.569 of refractive index, 35 of Abbé's number, 91 % transmittance (550 nm), 2H of pencil hardness, a high impact resistance which passed inspection of FDA Standard, a good solvent resistance, a good dyeability, a good adhesion of coating glass film, and such a good workability that cutting and grinding it can be easily carried outO
Example 2 - 11, Comparative Example 1 - 2 The lenses were made in ~he same manner as in Example 1, except that conditions in Table 1 were used.
The result is shown in Table 1.
7~
_ ~ ~
.' ~ ~1 O O ~ O O O O O O X X
~0 rD
. _. _ . _ . .. _ . .. . __ ~oo . O O C) O O O O ~ O O O X X
~o~ ¢
_ .____ I
~..
V) ~ ~ ~ ~ O O C) O X 'X
o ~ ~
P~ ~d .. ~ .
~H V) o ,, ~
~ t~ ~ ~ C X
a> ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ X
.,,~ ~
~ P~ :C
o u~ h P~- a,.
O -~D ~ u~ u~u~ In ~ ~ u~ Lr~ ~ U7 ~ a ,~
~ ~ ~ 1~ ~ t~lt~ t~ t~ ~ ~ t~ tJ~ t~
P~¢ ~::
_ __ _ _ . ~ o CO C7~ o o o ,~ ~ oo o ~ ~
"D ~ ~ ~ I~ 1~ 1~ t` ~ ~D r~oo co u~
~ ~ ~::
.D IY ~
~ ~ ~ ~ ~ ,1 0 ,1 0 cn ~1 0 o~ cr, O\o ~cn o~
Ll~ ~
~ - ~
O I
,l ~ ~ o --~ o ~ o .,~ o o ~ o a~ o v~ ,~ r~ oo ~ t~
o o o o o ~ ~ o ~ o ~
I~ oo O O ~1 O ~ ~ ~ ~ t~
P~ ~ P. ~ E~ P~ ~ ~
h ~ ~. P. ~ ¢ ~ ¢ ~ P~ ¢ ,~ h E~ ¢ ¢ ¢ ¢ ~ ~ ¢ ~ ~ C ~ h o ~ ~ ~ a c ¢ ~ ¢ ~
O ~ ~ t~ ~ ~ ~ ~ ~ ~ ~ ~ O O
- - - - -~ - l ~
~_( ~ t~ D t` 00 ~
x x w ~
~'7 Note 1.
CQPhMA : o-chlorophenyl methacrylate, CQBzMA : o-chlorobenzyl met}lacTylate, CQ5PhMA : pentachlorophenyl me~hacryla~e, PhMA : phenyl methacrylate, BrPhMA : p-bromophenyl methacrylate, Br3PhMA : 2,4,6-tribromophenyl methacrylate~
TAIC : triallylisocyanurate, DATP : diallylterephthalate, TAC : triallylcyanurate, DAIP : diallylisophthalate, BzMA : benzyl methacrylate Note 2.
Transmittance (%) : measured at 550 nm light using the lens of 2.0 mm thickness, Refractive Index, and Abbé's Number: measured by Abbe's refractometer, Pencil Hardness: measured by JIS K5400 Solvent Resistance: by immersing it in acetone, methanol, and benzene for 24 hours O : the surface did not become dull, X the surface became dull, Workabili~y: O : can be ground by lens grinder, X : can not be ground by lens grinder.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
As the polyfunctional allyl monomer of this invention are cited diallylorthophthalate, diallylisophth~late, diallylterephthalate, diallylchlorendate, triallylcyanurate, triallylisocyanurate 7 etc. They can be used 501ely or in ~3 ~7~
a mixture of two or more. In the mixture of diallyl monomer and triallyl monomer, triallyl monomer is preferably used in an amount of at mos~ 10 wt.%. The use of triallyl monomer in an amount more than 10 wt.~ is practically unfavorable, because of lowering the impact resistance of the lens obtained therefrom.
The lens of this in~ention can be prepared by the method comprising pouring the mixed solution consisting of above-said monomers and a polymerizatîon initiator into a mold mad0 of two plates of glass mold and a plastic gasket, and ~hen heating or irradiating with ultraviolet ray the resulting one.
The lens of this invention has an improved dispersion compared with well known lens made from polycarbonate or polystyrene, so that very l;ttle chromatic aberration appears in spite of the high refractive index in the lens 9 which is one of the features of this invention. The superficial hardness 3 solvent resistance, and workability thereof are considerably superior to those of polycarbonate lens or polystyrene lens. Coating glass film thereon by vacuum evaporation coating method can be easily effected, so that the ability of anti-reflectlon of the lens is excellent.
This invention will be more clearly understood with reference to the following Examples.
~ ~7~
Example 1 A mixed solution consisting of 30 wt. parts of phenyl methacrylate, 70 wt. parts of diallylisophthalate and 2.5 wt. parts of diisopropylperoxydicarbonate was poured into a mold made of two plates of glass mold, and a gasket of ethylene-vinylacetate copolymer, and the resulting one was heated to raise gradually the temperatur~ from 40C to 90C in 24 hours. After end of the polymerization, the lens was taken out of the mold, and then was post-cured at 120C
for one hour. The resulting lens had 1.569 of refractive index, 35 of Abbé's number, 91 % transmittance (550 nm), 2H of pencil hardness, a high impact resistance which passed inspection of FDA Standard, a good solvent resistance, a good dyeability, a good adhesion of coating glass film, and such a good workability that cutting and grinding it can be easily carried outO
Example 2 - 11, Comparative Example 1 - 2 The lenses were made in ~he same manner as in Example 1, except that conditions in Table 1 were used.
The result is shown in Table 1.
7~
_ ~ ~
.' ~ ~1 O O ~ O O O O O O X X
~0 rD
. _. _ . _ . .. _ . .. . __ ~oo . O O C) O O O O ~ O O O X X
~o~ ¢
_ .____ I
~..
V) ~ ~ ~ ~ O O C) O X 'X
o ~ ~
P~ ~d .. ~ .
~H V) o ,, ~
~ t~ ~ ~ C X
a> ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ X
.,,~ ~
~ P~ :C
o u~ h P~- a,.
O -~D ~ u~ u~u~ In ~ ~ u~ Lr~ ~ U7 ~ a ,~
~ ~ ~ 1~ ~ t~lt~ t~ t~ ~ ~ t~ tJ~ t~
P~¢ ~::
_ __ _ _ . ~ o CO C7~ o o o ,~ ~ oo o ~ ~
"D ~ ~ ~ I~ 1~ 1~ t` ~ ~D r~oo co u~
~ ~ ~::
.D IY ~
~ ~ ~ ~ ~ ,1 0 ,1 0 cn ~1 0 o~ cr, O\o ~cn o~
Ll~ ~
~ - ~
O I
,l ~ ~ o --~ o ~ o .,~ o o ~ o a~ o v~ ,~ r~ oo ~ t~
o o o o o ~ ~ o ~ o ~
I~ oo O O ~1 O ~ ~ ~ ~ t~
P~ ~ P. ~ E~ P~ ~ ~
h ~ ~. P. ~ ¢ ~ ¢ ~ P~ ¢ ,~ h E~ ¢ ¢ ¢ ¢ ~ ~ ¢ ~ ~ C ~ h o ~ ~ ~ a c ¢ ~ ¢ ~
O ~ ~ t~ ~ ~ ~ ~ ~ ~ ~ ~ O O
- - - - -~ - l ~
~_( ~ t~ D t` 00 ~
x x w ~
~'7 Note 1.
CQPhMA : o-chlorophenyl methacrylate, CQBzMA : o-chlorobenzyl met}lacTylate, CQ5PhMA : pentachlorophenyl me~hacryla~e, PhMA : phenyl methacrylate, BrPhMA : p-bromophenyl methacrylate, Br3PhMA : 2,4,6-tribromophenyl methacrylate~
TAIC : triallylisocyanurate, DATP : diallylterephthalate, TAC : triallylcyanurate, DAIP : diallylisophthalate, BzMA : benzyl methacrylate Note 2.
Transmittance (%) : measured at 550 nm light using the lens of 2.0 mm thickness, Refractive Index, and Abbé's Number: measured by Abbe's refractometer, Pencil Hardness: measured by JIS K5400 Solvent Resistance: by immersing it in acetone, methanol, and benzene for 24 hours O : the surface did not become dull, X the surface became dull, Workabili~y: O : can be ground by lens grinder, X : can not be ground by lens grinder.
Claims
1. A lens having a low dispersion and a high refractive index prepared from the copolymer obtained by copolymerizing polyfunctional allyl monomer with at least one selected from the monomer group represented by the general formula A
...................... A
X : H, CH3, C?
Y : H, CH3, C2H5, n-C3H7, iso-C3H7, OCH3, C6H11, C? Br, CH2C?, CH2Br, C6H5, CH2C6H5,SCH3 m : 0, 1, 2 n : 0, 1, 2, 3, 4, 5.
...................... A
X : H, CH3, C?
Y : H, CH3, C2H5, n-C3H7, iso-C3H7, OCH3, C6H11, C? Br, CH2C?, CH2Br, C6H5, CH2C6H5,SCH3 m : 0, 1, 2 n : 0, 1, 2, 3, 4, 5.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55175779A JPS6017404B2 (en) | 1980-12-15 | 1980-12-15 | Low dispersion high refractive index lens |
| JP175779/1980 | 1980-12-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1167198A true CA1167198A (en) | 1984-05-08 |
Family
ID=16002110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000388393A Expired CA1167198A (en) | 1980-12-15 | 1981-10-21 | Lens having a high refractive index with a low dispersion |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4393184A (en) |
| JP (1) | JPS6017404B2 (en) |
| AU (1) | AU543708B2 (en) |
| CA (1) | CA1167198A (en) |
| DE (1) | DE3146075C2 (en) |
| FR (1) | FR2496278A1 (en) |
| GB (1) | GB2089523B (en) |
| IT (1) | IT1140337B (en) |
| NL (1) | NL8105059A (en) |
| SE (1) | SE450882B (en) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58167125A (en) * | 1982-03-29 | 1983-10-03 | Nippon Oil & Fats Co Ltd | Manufacture of plastic lens |
| JPS58167124A (en) * | 1982-03-29 | 1983-10-03 | Nippon Oil & Fats Co Ltd | Manufacture of plastic lens |
| DE3216988A1 (en) * | 1982-05-06 | 1983-11-10 | Chemische Werke Hüls AG, 4370 Marl | POLYMERS PHENYLALKYL ACRYLIC ACID ESTERS, THEIR PRODUCTION AND THEIR USE |
| EP0112927B1 (en) * | 1982-07-08 | 1987-02-11 | MITSUI TOATSU CHEMICALS, Inc. | Resin for lens with high refractive index and lens composed of it |
| JPS5996113A (en) * | 1982-11-25 | 1984-06-02 | Mitsui Toatsu Chem Inc | Resin for high-refractive index lens |
| JPS598709A (en) * | 1982-07-08 | 1984-01-18 | Mitsui Toatsu Chem Inc | Resin for lens having high refractive index |
| DE3248601A1 (en) * | 1982-12-30 | 1984-07-12 | Röhm GmbH, 6100 Darmstadt | POLYMERISATE WITH LOW WATER ABSORPTION |
| EP0312120B1 (en) * | 1982-12-30 | 1992-03-04 | Röhm Gmbh | Process for preparing moulding materials of acrylic resins with slight water absorption |
| DE3248602A1 (en) * | 1982-12-30 | 1984-07-12 | Röhm GmbH, 6100 Darmstadt | ACRYLIC RESINS WITH LOW WATER ABSORPTION |
| US4616045A (en) * | 1983-06-23 | 1986-10-07 | Gbf, Inc. | Process of preparing an oxygen permeable, styrene based, contact lens material |
| US4528301A (en) * | 1983-06-23 | 1985-07-09 | Gbf, Inc. | Oxygen permeable, styrene based, contact lens material |
| CA1252249A (en) * | 1983-09-24 | 1989-04-04 | Teruo Sakagami | Halogen-containing resin lens material |
| JPS6069114A (en) * | 1983-09-24 | 1985-04-19 | Kureha Chem Ind Co Ltd | Halogen-containing resinous lens material |
| DE3563001D1 (en) * | 1984-01-27 | 1988-07-07 | Mitsubishi Rayon Co | Plastic lens and method of manufacturing thereof |
| JPS60197709A (en) * | 1984-03-19 | 1985-10-07 | Ito Kogaku Kogyo Kk | Organic glass for optical part |
| FR2565699A1 (en) * | 1984-06-11 | 1985-12-13 | Suwa Seikosha Kk | METHOD OF MODIFYING THE SURFACE OF A BASE MATERIAL COMPRISING CARBONATE AND ALLYL ESTER PATTERNS TO FORMALLY FORM A HARD SURFACE COATING IN THE CASE OF LENSES FOR OPHTHALMIC GLASSES |
| US4774293A (en) * | 1985-06-26 | 1988-09-27 | Akzo N.V. | Process for cross-linking or degrading polymers and shaped articles obtained by this process |
| CA1239739A (en) * | 1985-07-19 | 1988-07-26 | Hideo Nakamoto | Plastic lens |
| US4693446A (en) * | 1985-09-20 | 1987-09-15 | Techna Vision, Inc. | Gasket for molding plastic lenses |
| DE3636399A1 (en) * | 1986-10-25 | 1988-05-05 | Hoechst Ag | OPTICAL FIBER |
| DE3636401A1 (en) * | 1986-10-25 | 1988-04-28 | Hoechst Ag | TRANSPARENT POLYMER MATERIAL |
| DE3636400A1 (en) * | 1986-10-25 | 1988-05-05 | Hoechst Ag | TRANSPARENT POLYMER MATERIAL |
| JP2515010B2 (en) * | 1989-01-26 | 1996-07-10 | 株式会社メニコン | Ophthalmic lens material |
| US5290892A (en) * | 1990-11-07 | 1994-03-01 | Nestle S.A. | Flexible intraocular lenses made from high refractive index polymers |
| ES2094796T3 (en) * | 1990-11-07 | 1997-02-01 | Nestle Sa | POLYMERS AND THEIR USE FOR OPHTHALMIC LENSES. |
| US5294484A (en) * | 1991-08-03 | 1994-03-15 | Sony Corporation | Polyvinyl aromatic carboxylic acid ester and video printing paper |
| EP0774983B1 (en) * | 1995-06-07 | 2002-12-04 | Alcon Laboratories, Inc. | Improved high refractive index ophthalmic lens materials |
| US5922821A (en) * | 1996-08-09 | 1999-07-13 | Alcon Laboratories, Inc. | Ophthalmic lens polymers |
| US5932626A (en) * | 1997-05-09 | 1999-08-03 | Minnesota Mining And Manufacturing Company | Optical product prepared from high index of refraction brominated monomers |
| US6355754B1 (en) | 1997-05-09 | 2002-03-12 | 3M Innovative Properties Company | High refractive index chemical composition and polymers and polymeric material derived therefrom |
| US6107364A (en) * | 1997-05-09 | 2000-08-22 | 3M Innovative Properties Company | Methyl styrene as a high index of refraction monomer |
| JP5459816B2 (en) | 1999-09-07 | 2014-04-02 | アルコン，インコーポレイテッド | Foldable ophthalmic and otolaryngological device materials |
| US6703466B1 (en) * | 2001-06-18 | 2004-03-09 | Alcon, Inc. | Foldable intraocular lens optics having a glassy surface |
| US20050085908A1 (en) * | 2003-10-20 | 2005-04-21 | Chang Yu-An | New ophthalmic lens materials with high refractive index and biocompatible surface |
| DE102008035576A1 (en) * | 2008-07-30 | 2010-02-04 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Photovoltaic device and method for producing a concentrator optics |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2855434A (en) * | 1956-01-05 | 1958-10-07 | Pittsburgh Plate Glass Co | Method for preparing unsaturated aromatic compounds |
| BE600675A (en) * | 1960-02-29 | |||
| DE2730370A1 (en) * | 1977-07-05 | 1979-01-25 | Agfa Gevaert Ag | Copolymers of cyclohexyl methacrylate! and maleic anhydride! - for use in lenses, giving improved heat stability and water resistance |
| JPS5817527B2 (en) * | 1978-07-17 | 1983-04-07 | 株式会社保谷レンズ | Copolymers for high refractive index lenses and lenses made from them |
-
1980
- 1980-12-15 JP JP55175779A patent/JPS6017404B2/en not_active Expired
-
1981
- 1981-10-21 CA CA000388393A patent/CA1167198A/en not_active Expired
- 1981-10-26 US US06/315,354 patent/US4393184A/en not_active Expired - Lifetime
- 1981-11-09 NL NL8105059A patent/NL8105059A/en not_active Application Discontinuation
- 1981-11-20 DE DE3146075A patent/DE3146075C2/en not_active Expired
- 1981-11-27 FR FR8122314A patent/FR2496278A1/en active Granted
- 1981-12-11 SE SE8107433A patent/SE450882B/en not_active IP Right Cessation
- 1981-12-14 AU AU78491/81A patent/AU543708B2/en not_active Ceased
- 1981-12-14 GB GB8137660A patent/GB2089523B/en not_active Expired
- 1981-12-15 IT IT25613/81A patent/IT1140337B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| AU543708B2 (en) | 1985-04-26 |
| IT1140337B (en) | 1986-09-24 |
| SE450882B (en) | 1987-08-10 |
| FR2496278B1 (en) | 1984-12-28 |
| JPS5799601A (en) | 1982-06-21 |
| US4393184A (en) | 1983-07-12 |
| GB2089523B (en) | 1984-05-31 |
| JPS6017404B2 (en) | 1985-05-02 |
| IT8125613A0 (en) | 1981-12-15 |
| NL8105059A (en) | 1982-07-01 |
| DE3146075C2 (en) | 1985-09-19 |
| FR2496278A1 (en) | 1982-06-18 |
| SE8107433L (en) | 1982-06-16 |
| AU7849181A (en) | 1982-06-24 |
| DE3146075A1 (en) | 1982-06-24 |
| GB2089523A (en) | 1982-06-23 |
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