MXPA00001606A - Optic devices formed from melt processable thermoplastic materials having a high refractive index - Google Patents
Optic devices formed from melt processable thermoplastic materials having a high refractive indexInfo
- Publication number
- MXPA00001606A MXPA00001606A MXPA/A/2000/001606A MXPA00001606A MXPA00001606A MX PA00001606 A MXPA00001606 A MX PA00001606A MX PA00001606 A MXPA00001606 A MX PA00001606A MX PA00001606 A MXPA00001606 A MX PA00001606A
- Authority
- MX
- Mexico
- Prior art keywords
- lens
- further characterized
- preform
- ophthalmic
- blank
- Prior art date
Links
- 239000012815 thermoplastic material Substances 0.000 title claims description 5
- 230000000750 progressive effect Effects 0.000 claims abstract description 4
- 229920000642 polymer Polymers 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 9
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 6
- 229930185605 Bisphenol Natural products 0.000 claims description 5
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000000463 material Substances 0.000 description 13
- 230000003287 optical effect Effects 0.000 description 9
- 229920000570 polyether Polymers 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- SLIPRCNBMAJHPZ-UHFFFAOYSA-N FC1=CC=CC=C1P(=O)C1=CC=CC=C1 Chemical compound FC1=CC=CC=C1P(=O)C1=CC=CC=C1 SLIPRCNBMAJHPZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 description 1
- LSQARZALBDFYQZ-UHFFFAOYSA-N 4,4'-difluorobenzophenone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 LSQARZALBDFYQZ-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012768 molten material Substances 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical group C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
Abstract
This invention relates generally to optic devices such as lenses, (monofocal and multifocal), progressive lenses, lens blanks, and lens preforms having a specific formula.
Description
OPTICAL DEVICES AND MATERIALS OF THERMOPLASTIC MATERIALS WITH HIGH REFRACTION INDEX
CAN PROCESS UNDER FUSION
FIELD OF THE INVENTION
This invention relates generally to optical devices such as lenses (monofocal and multifocal), progressive lenses, lens blanks and lens preforms.
BACKGROUND OF THE INVENTION
Lenses formed of thermoplastic material are becoming more common. Advances in the production of such lenses have included the use of lighter materials and free of unwanted color. An attractive and important way to optimize a plastic lens is by using materials that have a high refractive index. This allows lens designers to design thinner lenses that have surfaces with larger radii of curvature. Aromatic thermoplastics have been recognized as potential candidates for the manufacture of materials with high refractive index for optical applications, particularly in the area of eyeglass use. Aromatic polycarbonates typify this approach to optical applications and have a refractive index of about 1.59. However, it is known that these materials are subject to undesirable chromatic aberration. Aromatic polyethers containing the triphenylphosphine oxide moiety in the repeating unit have been described in the literature. Aromatic polyethers containing the phosphine oxide group are shown or suggested and described in U.S. Patent Nos. 4,108,837 and 4,175,175. Some work has been attempted on the use of these materials as short-range optical fibers, and plasma-resistant coatings. These materials can be synthesized by reaction of a variety of bisphenols with 4,4'-bis (fluorophenyl) phenylphosphine oxide (BFPPO) in the presence of a base such as potassium carbonate in dipolar aprotic solvents such as N-methylpyrrolidinone ( NMP) or N, N-dimethylacetamide (DMAC). Techniques for the synthesis of these compounds are known and many of their physical properties are well documented in the literature. See, for example, C.D., Smith, et al. SAMPE Symps Exib. Vol. 35, No. 1, pp. 108-22 (1990); R. L. Holzberlein, et al, Polymer Prepr.,. Vol. 30, No. 1 p, 293 (1989); D. B. Priddy, et al, Polymer Prepr., Vol. 34, No. 1, pp. 310-11 (1993); D.B. Priddy et al, Polimer Prepr. Vol. 33, No.2, pp. 231-32 (1992); CD. Smith, et al., Polymer Prepr., Vol. 32, No. 1, pp. 93-5 (1991); CD. Smith, et al, High Perform. Polymers, Vol. 3, No. 4, pp, 221-29 (1991). Controlled molecular weight can be generated with non-reactive end groups, for example, by employing a monofunctional monomer such as 4, tert-butyl phenol.
BRIEF DESCRIPTION OF THE INVENTION
The present invention relates to optical devices formed of phosphine oxide containing aromatic polyethers and copolymers with non-reactive end groups. These polyethers of controlled molecular weight show good mechanical properties as well as favorable optical properties such as a refractive index of at least 1.63, good clarity, and light color. This is decisive for the development of good quality, thin and lightweight ophthalmic lenses. Optical devices made of these materials are also less subject to chromatic aberrations. It is believed that the non-reactive chain ends help to maintain a stable melt viscosity during the operation of the process, and that there is no change in the viscosity of the melt due to chain extension or branching during the process, which It also leads to loss of optical properties. The superior thermomechanical stability of these materials allows them to be processed at fairly high temperatures without thermal and mechanical deterioration.
^ wjg í DETAILED DESCRIPTION OF THE INVENTION
The aromatic polyethers that contain the portion Phosphine oxide in the base structure of the polymer chain possesses the decisive properties for its successful application in the area of ophthalmic lenses for spectacle use. The presence of the phosphine oxide moiety in the base structure of the polymer chain contributes to a higher refractive index as well as improved thermal and mechanical properties. These materials show high glass transition temperatures on the 200-225 ° C scale and therefore have to be processed at elevated temperatures such as 325-350 ° C. The mechanical properties of these materials indicate that they are hard, ductile and even crystalline under environmental conditions and therefore, facilitate the production of thin lenses that have good resistance to impacts. A non-reactive and appropriately blocked phosphine oxide at the end which contains aromatic polyether is described as the formula I shown below:
where n =, 20 to 200, preferably 30-70.
The polymer can be formed by reacting BFPPO, bisphenol 'A' and a 4-tert-butylphenol shown below, under the conditions described in example 1.
Other homopolymers can be generated by using a variety of bisphenols in place of bisphenol 'A' such as hydroquinone, biphenol, 4,4'-oxypi phenol or bis (4-hydroxyphenyl) sulfone. A series of polyether copolymers can be provided by replacing part of the phosphine oxide monomer with either 4,4'-dichlorodiphenylsulfone or 4,4'-difluorobenzophenone. The general structure of said copolymers can be shown in the following manner.
where n = 20 to 200, preferably 30-70,
where R = -H,
OR
II O -s- II [0-90% molar] _C - [0-90% molar] or
However, anhydrous morphologies must be maintained. Optical devices made of these materials are optically clear, and thinner at their edges than conventional ophthalmic plastic lenses because of their higher refractive index values.
. ^. ^ - A-J-M- ..
EXAMPLE 1 (Preparation of the Polymer)
31. 43 grams (0.1 moles) of 4,4'-bis (fluorophenyl) phenyl-phosphine oxide (BFPPO) [molecular weight = 314.2706] together with 22.25 grams (0.098 moles) of bifengol 'A' [molecular weight = 228.2902] together with 0.70 (0.005 moles) of 4-ter, butylphenol [molecular weight = 138.209] were charged to a four-necked flask for reaction adapted with a bubbling device for argon, an upper mechanical stirrer and a Dean-Stark trap connected to a reflux condenser. The reagents were dissolved in enough DMAC to form a 30% by weight solution in a mixture of DMAC and chlorobenzene (80:20). Chlorobenzene served to function as an azeotropic solvent to efficiently remove water from the condensation reaction as it formed during polymerization. The reaction was initially held at 135-140 ° for 4 hours until the condensation water was distilled completely. Subsequently, the reaction temperature was gradually raised to about 165 ° C and held there for another 16 hours. The reaction product was then allowed to cool to room temperature and filtered to remove inorganic salts and neutralized with glacial acetic acid, also isolated by precipitation into a rapidly stirred methanol / water mixture in a high-speed mixer. speed. Then the precipitated polymer was filtered and dried in a vacuum oven at
^ g ^ a ^ is approximately 200 ° C overnight after being repeatedly washed with methanol to remove all traces of solvent. The preferred scale of number average molecular weight for these polymers is about 15000-25000 g / mol. At a number average molecular weight greater than 25,000 g / mol, the viscosity of the molten material may be too high for a rapid process. Therefore, the polymers have been synthesized with a target molecular weight of 20000 g / mol. It is known from the literature that the length of the polymer chain, and therefore the molecular weight of the polymer can be adjusted by controlling the proportion of phosphine oxide to aryl portions used in the synthesis process.
EXAMPLE 2 (Lens formation)
A single viewing lens of 80 mm diameter with a refractive index of 1.66, a spherical increase of -6.00 D to a central thickness of 1.00 mm is made from the polymer of Example 1 by processing the molten polymer by an extruder and then forming a lens of the extruded material heated in a conventional injection molding apparatus. The thickness of the edge for said lens is 8.8 mm. A corresponding high index lens made of polycarbonate having a refractive index of 1.58 under the same series of parameters (ie, central thickness of 1.0 mm, spherical increase of 6.00 D, and lens diameter of 80 mm.) Would have a thickness of 10.0 mm on the edge. The above non-limiting example is given as an illustration. The scope of the present invention is defined solely by the following claims.
^^ m mi ^^ m
Claims (15)
1. - An ophthalmic lens, lens primer or lens preform that
It consists of a thermoplastic material of the formula: where n = 20 to 200, R is hydrogen,
Ar is 0 or 0-90% molar j I ciI - - 2.- The ophthalmic lens, lens blank or lens preform according to claim 1, further characterized in that the molecular weight of the polymer is from about 15,000 to about 25,000. 3. The ophthalmic lens, lens blank or lens preform according to claim 1, further characterized in that the molecular weight of the polymer is approximately 20,000.
4. The ophthalmic lens, lens primer or lens preform according to claim 1, further characterized in that the thermoplastic material is of the formula: where n = 30 to 70.
5. The ophthalmic lens according to claims 1, 2, 3 or 4, further characterized in that the lens is a spectacle lens.
6. The ophthalmic lens, lens blank or lens preform according to claims 1, 2, 3 or 4, further characterized in that the lens blank is a lens primer of eyeglasses.
7. The ophthalmic lens, lens blank, or lens preform according to claims 1, 2, 3 or 4, further characterized in that the lens prefix is a spectacle lens preform.
8. The ophthalmic lens, lens blank, or lens preform according to claims 1, 2, 3 or 4, further characterized in that the lens is a progressive spectacle lens.
9. The ophthalmic lens, lens blank, or lens preform according to claims 1, 2, 3 or 4, further characterized in that the lens is a bifocal eyeglass lens
10. A method for forming an ophthalmic lens, lens blank, or lens preform consisting of the passage in which a phosphine oxide portion and a cyclic aryl portion, a bicyclic aryl portion, or mixtures thereof are polymerized.
11. The process according to claim 10, further characterized in that the aryl portion is a mixture of bisphenol and butylphenol. 12.-. The method according to claim 10 or 11, further characterized in that the lens is a spectacle lens. 13. The method according to claim 10 or 11, further characterized in that the lens blank is a lens primer of eyeglasses. 14. The method according to claim 10 or 11, further characterized in that the lens preform is a spectacle lens preform. 15. The method according to claim 12, further characterized in that the spectacle lens is a progressive lens.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08912117 | 1997-08-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA00001606A true MXPA00001606A (en) | 2001-11-21 |
Family
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