CN1513006A - Resin compositions, and optical lens prepared thereby - Google Patents
Resin compositions, and optical lens prepared thereby Download PDFInfo
- Publication number
- CN1513006A CN1513006A CNA028110765A CN02811076A CN1513006A CN 1513006 A CN1513006 A CN 1513006A CN A028110765 A CNA028110765 A CN A028110765A CN 02811076 A CN02811076 A CN 02811076A CN 1513006 A CN1513006 A CN 1513006A
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- compound
- methyl
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- 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
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- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The present invention relates to an optical resin composition comprising (A) 10-75 parts by weight of (meth)acrylate compound having bisphenol A structure represented as the formula 1, (B) 1-70 parts by weight of aliphatic polythiol compound represented as the formula 2, (C) 1-40 parts weight of (meth)acrylate compound having sulfur bond represented as the formula 3, and (D) 1-45 parts by weight of (meth)acrylate compound having aliphatic or alicyclic group represented as the formula 4. Further,the present invention provides an optical lens with a high refractive index, a high Abbe's number, and the excellent properties of transparency, optical homogeneity and lighweight by polymerization and curing the above composition.
Description
Technical field
The optical lens that the invention relates to a kind of resin combination and obtain by polymerization and curing.
Background technology
Plastic lens is compared with inorganic lenses, be lighter, be difficult to fragmentation and easier to be painted because this reason, they are widely used in the optical device field.
In being used as the resin of plastic lens material, glycol ether is the light weight of lens to the characteristics of (allyl carbonate), and this is because its proportion (1.32) is littler than (2.54) of unorganic glass.
Yet this plastics will have shortcoming thoroughly, for example compare with inorganic lenses, increase at center thickness and edge thickness, and this is because adopt the resulting refractive index (n of this resin
D 20=1.50) than the refractive index (n of unorganic glass lens
D 20=1.52) low.
In resin as plastic lens material with high index, poly-carbonic acid (n
D 20=1.58) and polyethylene (n
D 20=1.60) only only limit to during among a small circle optics uses, this is because they have following physicals: low polishing processibility, the low scratch resistance that causes because of surface hardness and low organic solvent resistance.
Resin as the plastic lens material with high index is (1) diacrylate or dimethacrylate [JP116301/83] from dihydroxyphenyl propane, (2) from the diacrylate or the dimethacrylate [JP10491/82] of halogenation dihydroxyphenyl propane, (3) halogenated styrenes monomer and multi-functional methacrylic compound [JP104101/82,28118/82,28116/82], (4) diallyl phthalic acid monomer [JP212401/82,15153/83].Yet it is 1.6 or three higher metanetworks that material 1 is difficult to form crosslinked refractive index, and decolouring in the time of the injection moulding polymeric easily in material (2), (3), (4), can not be satisfactory on the optical delivery of weatherability and visible light.
Therefore, be necessary to develop and a kind ofly be used for optical, can overcome above-mentioned shortcoming, have the high refractive index and the new type resin of high Abb.
The purpose of this invention is to provide a kind of resin combination that can solve the above problems and optical lens, above-mentioned resin combination can prepare the optical lens with high index, high Abb, high transparent, optics homogeneity and wavelength performance.
Summary of the invention
The invention provides a kind of optical resin composition, comprise
Compound (A): the methacrylic compound with the structure of bisphenol A shown in the general formula 1 of 10-75 weight part;
Compound (B): the aliphatic poly mercaptan compound shown in formula 2 of 1-70 weight part;
Compound (C): (methyl) acrylic compound of 1-40 weight part with the sulfide linkage shown in the formula 3; With
Compound (D): (methyl) acrylic compound of 1-45 weight part with the aliphatics shown in the formula 4 or aromatic group;
Formula 1
Wherein, R
1And R
2Be H or CH
3, each of m and n is the integer of 0-4, and the m+n scattering is 0-8, and Y is H or OH,
Formula 2
Wherein, when R is S or C, R
3And R
4Be CH
2SH, CH
2CH
2SH, COOCH
2SH, perhaps COOCH
2CH
2SH; When R is C, R
5And R
6Be CH
2SH; When R is S, R
5And R
6Do not exist.
Formula 3
Wherein, X is aliphatics or aromatic group, and Y is H or CH
3
Formula 4
Wherein, X is aliphatics or aromatic group, and Y is H or CH
3
Preferably, it is the 20-70 weight part that composition of the present invention comprises described compound (A), and compound (B) is the 1-20 weight part, and compound (C) is the 1-20 weight part, and compound (A) is the 1-15 weight part.
And, the invention provides a kind of optical lens with high refractive index, high Abbe number and good transparent, optics homogeneity and wavelength performance by above-mentioned composition being carried out polymerization and curing obtains.
The compound of optical resin composition of the present invention is as follows in detail:
(A) has (methyl) acrylic compound of the bis-phenol structure shown in the formula 1
Compound (A) has high refractive index, low viscosity, at least 2 functional groups.Because this functional group more than 2, compound (A) can free radical addition.
The free radical addition meaning be meant with sulphur be added to polyene compound or (methyl) acrylic compound unsaturated link(age) reaction or in the addition reaction of above-mentioned unsaturated link(age).
Preferably, compound (A) can be BPA-2A (diacrylate of the dihydroxyphenyl propane diepoxy third fat ether that oxyethane (2mol) adds), BPA-4EA (the dihydroxyphenyl propane diacrylate of oxyethane modification), BPA-4PA (the dihydroxyphenyl propane diacrylate of epoxy pronane modification), BPA-2EM (the dihydroxyphenyl propane diacrylate of oxyethane modification) etc.
Compound (A) is the 10-75 weight part in the quantity of total resin combination, is preferably the 20-70 weight part.
(B) the aliphatic poly mercaptan compound shown in the formula 2
Compound (B) is preferably the mercaptan compound that adds to above-claimed cpd A with 2 functional groups and energy free radical.
Preferably, compound (B) is DMDS (dimercapto two sulphur methane) and BMEE (two (2-ethane thiol) ether) etc.
Compound (A) is the 1-70 weight part in the quantity of total resin combination, is preferably the 1-20 weight part.
(C) has (methyl) acrylic compound of the sulfide linkage shown in the formula 3
Compound C can be free-radical polymerized with compd A.
Preferably, compound (C) is PTEA (a vinylformic acid benzene sulphur ethane), HTEMA (methacrylic acid hexyl sulphur ethane) and PTEEA (ethylacrylic acid benzene sulphur ethane) etc.
Compound (C) is the 1-40 weight part in the quantity of total resin combination, is preferably the 1-20 weight part.
(D) has (methyl) acrylic compound of aliphatics shown in the formula 4 or aromatic group
Compound D can be free-radical polymerized with compd A, B or C.
Preferably, compound (D) is DTDDA (dimethanol tristane diacrylate), HAPMA (2-hydroxyl-3-acryloyloxy) propyl methyl acid), and TMGDA (polytetramethylene ethylene glycol bisthioglycolate vinylformic acid) etc.
Compound (D) is the 1-45 weight part in the quantity of total resin combination, is preferably the 1-15 weight part.
Can join in the resin combination of the present invention such as the vinylbenzene of divinylbenzene, diisopropyl alkene benzene, vinylbenzene, nucleophilic substitution, (methyl) vinylformic acid etc. of simple function, purpose is the refractive index of control viscosity and resin combination.
More preferably, diluent is the o-divinylbenzene, the m-divinylbenzene, the p-divinylbenzene, m-diisopropyl alkene benzene, p-diisopropyl alkene benzene, vinylbenzene, vinyl toluene, chloro-styrene, dichlorostyrene, bromstyrol, Dowspray 9, (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) propyl acrylate, (methyl) isopropyl acrylate, (methyl) cyclohexyl acrylate, (methyl) phenyl acrylate, methyl) vinylformic acid phenoxy group ethane, (methyl) vinylformic acid Racemic glycidol, with Racemic glycidol propylene ether etc., more preferably, divinylbenzene and vinylbenzene.
If desired, various additives such as absorption agent, antioxidant, anti-jaundice agent (antiyellowingagent), tinting material, perfume compound, chain-transfer agent and releasing agent etc. can join in the resin combination of the present invention, purpose is to obtain needed physicals or function, only otherwise have retroaction just passable to effect of the present invention.
Optical lens with high index and high Abbe number can be by carrying out polymerization to composition of the present invention and curing obtains, wherein, and refractive index (n
D 20) should be at least greater than 1.59.
If desired, can anneal to optical lens after the curing (anneal).And, can carry out such as surface finish, antistatic treatment, be coated with, do not reflect the physics and the chemical treatment of coating, painted processing etc. firmly, purpose is in order to stop reflection and to improve the appearance of hardness and optical lens.
Optical lens of the present invention uses known radical polymerization by casting polymerization preparation.
Detailed says, joins in the resin combination of the present invention such as the catalyzer of radical polymerization initiator and Photoepolymerizationinitiater initiater etc., mixes, and filtering mixt under reduced pressure fully defoams, and is injected into to cause radical polymerization in the mould.
Mould can comprise, for example two templates of using polyester binder band or liner.Template can be glass-glass, glass-plastics, glass-metal sheet etc.
Preferably, be used for preparing the catalyzer of the polyreaction of optical lens, that is to say, radical polymerization initiator, can be known peralcohol, for example, benzoyl, p-benzoyl chloride superoxide, lauroyl peroxide, acetyl peroxide, di-t-butylperoxide, 1,1-two-t-crosses oxygen-butyl-3,3, the 5-trimethyl-cyclohexane, t-crosses the oxygen-butyl pivalate, t-crosses oxygen-butyl 2-ethyl hexanoate benzoic acid salt, two (4-t-butylcyclohexyl) sodium bicarbonates of peroxide, peroxide di-isopropyl sodium bicarbonate, cross for example mixture of Diisopropyl azodicarboxylate or these compounds of oxygen-butyl sec.-propyl sodium bicarbonate and nitrogenous compound with t-.
The quantity of catalyzer is the 0.001-5 weight part, is preferably the 0.01-3 weight part.
The quantity of above-mentioned compound determines according to the kind of polymeric temperature and time, employed radical polymerization initiator, the size of solidifying product etc.
After resin combination of the present invention joins mould, under 25-110 ℃, described composition is carried out polymerization and solidifies preparing optical lens of the present invention in 10-30 hour.
Embodiment
Embodiment 1
Under the condition of room temperature, 47g dihydroxyphenyl propane diacrylate, 15g hexyl sulphur ethane methacrylic acid, 5g 2-hydroxyl-3-acryloyloxyp propyl methyl acid, two (2-ethane thiol) ethers of 12g, 5g vinylbenzene, 16g divinylbenzene uniform mixing, 0.3g t-butyl peroxy sec.-propyl carbonic acid (t-butylperoxyisopropylcarbonate) is joined in the mixture, then mixture is joined in two glass templates, in 35-110 ℃ of following polymerization and curing 19 hours, after solidifying end, after being cooled to 40 ℃, from mould, remove the solidified product.Removed remaining pressure in 1-2 hour by the solidified product is annealed and obtain plastic lens under 90-110 ℃ of temperature.
Embodiment 2-5
Prepare plastic lens according to the compound concentrations shown in the table 1.By the technology as embodiment 1.
Comparative example
The dihydroxyphenyl propane methacrylic acid of 40g dihydroxyphenyl propane diacrylate, the addition of 21g oxyethane, 8g benzene sulphur ethyl-methyl vinylformic acid, 3g dimethanol tricyclic decane diacrylate, 10g vinylbenzene, 18g vinyl toluene uniform mixing obtain plastic lens by the described same casting polymerization technique of embodiment.
The test example
The physicals of the lens in embodiment 1-5 and the comparative example is following to be assessed.
(1) transparency: visual observation does not have be evaluated as " good " of color, confusion and distortion
(2) refractive index and Abbe number:, measure by the Pulfrich refractometer if measure the refractive index of prepolymer with Abbe refractometer.
(3) impact resistance: using the height of 28.5g steel ball at high 150cm, is that the lens of 1.5-1.6mm carry out falling sphere test (dropping-ball) to center thickness,, is evaluated as " O " if pass through, and, is evaluated as " X " if do not pass through.
(4) thermotolerance: pass with TMA and to measure lens in the mould.In the thermal flexure temperature is to be evaluated as " X ", " O " respectively below 80 ℃ and above 80 ℃.
(5) chromaticity (tintability): in painted groove, with glycol ether allyl carbonate is carried out paintedly to resin/lens,,, be evaluated as " X " if less than control if paintedly be equal to or, be evaluated as " O " greater than control.
(6) weathering: optical lens is placed in the weathering device that is provided with sunlight carbon one arc lamp, tested 200 hours, the color of specimen is compared with initial optical lens, if as broad as long, is evaluated as " O ", if flavescence is evaluated as " X ".
The mensuration physicals of lens is as shown in table 1.
| Compound | Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Embodiment 5 | Comparative example | |
| ?A | ?BPA-2A | ?55 | ?58 | ?40 | |||
| ?BPA-4EA | ?50 | ||||||
| ?BPA-4PA | ?47 | ||||||
| ?BPA-2EM | ?55 | ?21 | |||||
| ?B | ?DMDS | ?8 | ?10 | ?9 | |||
| ?BMEE | ?12 | ?10 | |||||
| ?C | ?PTEA | ?7 | ?10 | ||||
| ?HTEMA | ?15 | ?8 | |||||
| ?PTEEA | ?12 | ?8 | |||||
| ?D | ?DTDDA | ?3 | ?3 | ?3 | |||
| ?HAPMA | ?5 | ?5 | |||||
| ?TMGDA | ?3 | ||||||
| ?SM | ?5 | ?7 | ?7 | ?5 | ?10 | ?10 | |
| ?DVB | ?16 | ?20 | ?15 | ?10 | ?15 | ||
| ?VT | ?5 | ?18 | |||||
| Refractive index (n D 20) | ?1.591 | ?1.595 | ?1.593 | ?1.589 | ?1.595 | ?1.588 | |
| Physicals | Abbe number (v D 20) | ?38.0 | ?34.5 | ?35.0 | ?35.5 | ?35.0 | ?33.5 |
| Density (g/cm 3) | 1.14 | ?1.15 | ?1.15 | ?1.16 | ?1.14 | ?1.27 | |
| Impact resistance | O | ?O | ?O | ?O | ?O | ?X | |
| Weathering | X | ?O | ?O | ?X | ?O | ?X | |
| Chromaticity | O | ?O | ?O | ?O | ?O | ?X | |
| Thermotolerance | X | ?O | ?X | ?O | ?X | ?X |
*BPA-2A: the diacrylate of the dihydroxyphenyl propane diepoxy third fat ether of oxyethane (2mol) addition
*BPA-4EA: the diacrylate of the dihydroxyphenyl propane of oxyethane modification
*BPA-4PA: the diacrylate of the dihydroxyphenyl propane of epoxy pronane modification
*BPA-2EM: the dimethacrylate of the dihydroxyphenyl propane of oxyethane modification
*DMDS: dimercapto two thiomethyls
*BMEE: two (2-ethane thiol) ether
*PTEA: benzene sulphur ethane vinylformic acid
*HTEMA: hexyl sulphur ethane vinylformic acid
*PTEEA: benzene sulphur ethane ethane vinylformic acid
*DTDDA: dimethanol tricyclic decane diacrylate
*HAPMA:2-hydroxyl-3 acryloyloxyp
Propyl methyl acid
*TMGDA: poly-tetramethylethylene glycol diacrylate
*SM: styrene monomer
*DVB: divinylbenzene
*VT: vinyl toluene
As shown in table 1, by the prepared optical lens of the method shown in embodiment 1-5 tool not only
High refractive index and high Abbe number are arranged, and be good in anti-collision performance, windproof voltinism, chromaticity and thermotolerance.
The density of solidifying product of the present invention is 1.14-1.16, is lower than the density of CR-39 (1.32) and dimethyl aromatic base phosphorus benzene bis-acid potassium (1.22), and therefore, solidifying product of the present invention is suitable for preparing and has the optical lens lighter than existing commerical prod.
Commercial Application
The present invention can provide a kind of resin combination and by resin combination is carried out polymerization and curing, and the optical lens that obtains; This optical lens has high refractive index, high Abbe number, the good transparency, optics homogeney, lightweight.
Claims (8)
1. optical resin constituent comprises:
Compound (A): the methacrylic compound with the structure of bisphenol A shown in the general formula 1 of 10-75 weight part;
Compound (B): the aliphatic poly mercaptan compound shown in formula 2 of 1-70 weight part;
Compound (C): (methyl) acrylic compound of 1-40 weight part with the sulfide linkage shown in the formula 3; With
Compound (D): (methyl) acrylic compound of 1-45 weight part with the aliphatics shown in the formula 4 or aromatic group;
Formula 1
Wherein, R
1And R
2Be H or CH
3, each of m and n is the integer of 0-4, and the m+n scattering is 0-8, and Y is H or OH,
Formula 2
Wherein, when R is S or C, R
3And R
4Be CH
2SH, CH
2CH
2SH, COOCH
2SH, perhaps COOCH
2CH
2SH; When R is C, R
5And R
6Be CH
2SH; When R is S, R
5And R
6Do not exist.
Formula 3
Wherein, X is aliphatics or aromatic group, and Y is H or CH
3
Formula 4
Wherein, X is aliphatics or aromatic group, and Y is H or CH
3
2. optical resin composition as claimed in claim 1 is characterized in that, described compound (A) is the 20-70 weight part, and compound (B) is the 1-20 weight part, and compound (C) is the 1-20 weight part, and compound (A) is the 1-15 weight part.
3. as claim 1 or 2 described optical resin compositions, it is characterized in that described compound (A) is selected from BPA-2A (diacrylate of the dihydroxyphenyl propane diepoxy third fat ether of oxyethane (2mol) addition), BPA-4EA (the dihydroxyphenyl propane diacrylate of oxyethane modification), BPA-4PA (the dihydroxyphenyl propane diacrylate of epoxy pronane modification), BPA-2EM (the dihydroxyphenyl propane diacrylate of oxyethane modification).
4. as claim 1 or 2 described optical resin compositions, it is characterized in that compound (B) is selected from DMDS (dimercapto two sulphur methane) and BMEE (two (2-ethane thiol) ether)
5. as claim 1 or 2 described optical resin compositions, it is characterized in that compound (C) is selected from PTEA (benzene sulphur ethane vinylformic acid), HTEMA (hexyl sulphur ethane methacrylic acid) and PTEEA (benzene sulphur ethane ethylacrylic acid).
6. as claim 1 or 2 described optical resin compositions, it is characterized in that, compound (D) is selected from DTDDA (dimethanol tristane diacrylate), HAPMA (2-hydroxyl-3-acryloyloxy) propyl methyl acid), and TMGDA (polytetramethylene ethylene glycol bisthioglycolate vinylformic acid).
7. as claim 1 or 2 described optical resin compositions, it is characterized in that diluent is selected from the o-divinylbenzene, the m-divinylbenzene, the p-divinylbenzene, m-diisopropyl alkene benzene, p-diisopropyl alkene benzene, vinylbenzene, vinyl toluene, chloro-styrene, dichlorostyrene, bromstyrol, Dowspray 9, (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) propyl acrylate, (methyl) isopropyl acrylate, (methyl) cyclohexyl acrylate, (methyl) interior olefin(e) acid phenyl ester, methyl) vinylformic acid phenoxy group ethane, (methyl) vinylformic acid Racemic glycidol, with Racemic glycidol propylene ether.
8. the optical lens that any described composition of claim 1-7 is carried out polymerization and curing and obtain.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20010030477 | 2001-05-31 | ||
| KR2001/30477 | 2001-05-31 | ||
| KR10-2002-0029174A KR100477182B1 (en) | 2001-05-31 | 2002-05-27 | Resin compositions, and optical lens prepared by them |
| KR2002/29174 | 2002-05-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1513006A true CN1513006A (en) | 2004-07-14 |
Family
ID=26639113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA028110765A Pending CN1513006A (en) | 2001-05-31 | 2002-05-31 | Resin compositions, and optical lens prepared thereby |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN1513006A (en) |
| WO (1) | WO2002100911A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102250554A (en) * | 2011-05-23 | 2011-11-23 | 乐凯胶片股份有限公司 | Sealing adhesive film for solar cell |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10316671A1 (en) * | 2002-07-12 | 2004-01-22 | Röhm GmbH & Co. KG | Process for producing transparent plastics for optical materials |
| US7294657B2 (en) | 2005-03-07 | 2007-11-13 | General Electric Company | Curable acrylate compositions, methods of making the compositions and articles made therefrom |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2570776B2 (en) * | 1987-11-13 | 1997-01-16 | 三菱瓦斯化学株式会社 | Sulfur-containing aliphatic acrylic compound |
| JPH03121108A (en) * | 1989-07-18 | 1991-05-23 | Nippon Sheet Glass Co Ltd | Resin composition for optical material |
| JP2950877B2 (en) * | 1990-01-23 | 1999-09-20 | 三菱化学株式会社 | Monomer composition for producing optical resin and optical resin |
| JPH06211960A (en) * | 1993-01-14 | 1994-08-02 | Daiso Co Ltd | Polymerizable composition and high refractive index plastic lens obtained therefrom |
| JP3966577B2 (en) * | 1996-05-29 | 2007-08-29 | 三井化学株式会社 | Sulfur-containing O- (meth) acrylate compound, its production method and use |
| JP2000327754A (en) * | 1999-05-24 | 2000-11-28 | Seed Co Ltd | Synthetic resin-made lens |
-
2002
- 2002-05-31 CN CNA028110765A patent/CN1513006A/en active Pending
- 2002-05-31 WO PCT/KR2002/001034 patent/WO2002100911A1/en not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102250554A (en) * | 2011-05-23 | 2011-11-23 | 乐凯胶片股份有限公司 | Sealing adhesive film for solar cell |
| CN102250554B (en) * | 2011-05-23 | 2013-07-10 | 乐凯胶片股份有限公司 | Sealing adhesive film for solar cell |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002100911A1 (en) | 2002-12-19 |
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