GB1592724A - Polycarbonate optical lenses - Google Patents
Polycarbonate optical lenses Download PDFInfo
- Publication number
- GB1592724A GB1592724A GB879/78A GB87978A GB1592724A GB 1592724 A GB1592724 A GB 1592724A GB 879/78 A GB879/78 A GB 879/78A GB 87978 A GB87978 A GB 87978A GB 1592724 A GB1592724 A GB 1592724A
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- GB
- United Kingdom
- Prior art keywords
- bisphenol
- polycarbonate
- mol
- lens
- lenses
- 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.)
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- 239000004417 polycarbonate Substances 0.000 title claims description 38
- 229920000515 polycarbonate Polymers 0.000 title claims description 36
- 230000003287 optical effect Effects 0.000 title claims description 25
- 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 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 25
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 229930185605 Bisphenol Natural products 0.000 claims description 11
- 229940106691 bisphenol a Drugs 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 8
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 7
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 238000005259 measurement Methods 0.000 claims description 6
- 239000000155 melt Substances 0.000 claims description 6
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims description 5
- 239000011521 glass Substances 0.000 claims description 5
- 239000012074 organic phase Substances 0.000 claims description 5
- 239000012071 phase Substances 0.000 claims description 5
- -1 4,4'-dihydroxydiphenyl sulphide Chemical compound 0.000 claims description 4
- BATCUENAARTUKW-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-diphenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BATCUENAARTUKW-UHFFFAOYSA-N 0.000 claims description 4
- 239000006096 absorbing agent Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000003792 electrolyte Substances 0.000 claims description 4
- 238000006068 polycondensation reaction Methods 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 238000005809 transesterification reaction Methods 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 claims description 3
- 239000002216 antistatic agent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- OASFYFTVWALXTH-UHFFFAOYSA-L disodium;diphenoxide Chemical compound [Na+].[Na+].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OASFYFTVWALXTH-UHFFFAOYSA-L 0.000 claims description 2
- 230000009477 glass transition Effects 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229920003023 plastic Polymers 0.000 description 7
- 239000004033 plastic Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Lenses (AREA)
Description
(54) POLYCARBONATE OPTICAL LENSES
(71) We, BAYER AKTIENGESELLSCHAFT, a body corporate
organised under the laws of Germany, of Leverkusen, Germany, do hereby declare
the invention for which we pray that a patent may be granted to us, and the method
by which it is to be performed, to be particularly described in and by the following statement:- The invention relates to optical lenses made from an aromatic polycarbonate with relative viscosity 77 rel of 1.20 to 1.60 (measured in CH2Cl2 at 250C) and consisting of 15-100 mol V of structural units of the formula
and 85-0 mol % of structural units of the formula
wherein
R denotes
R' denotes -H, -CH3 or -Br, and in particular to high quality lenses for photographic cameras and cinecameras.
The polycarbonate has a refractive index nd of 1.59-1.66, preferably 1.60 1.66, an Able' number vd=29-22, preferably 27.5-22, and a colour triplet of 5.1; 0.1; 0, calculated according to DIN 4,522 part 5.
Optical systems, for example lenses for photographic cameras, have already been manufactured from transparent plastics. Only thermoplastic plastics are important in practice, because they can be processed economically and considerably better than glass. Thus, for example, polymethylmethacrylate is employed instead of silicate glasses of low refractive index. Polystyrene, copolymers of styrene and bisphenol A polycarbonate can also be used, predominantly for dispersing lenses.
The plastics mentioned can only be used for:
a) multi-lens objectives consisting only of plastic lenses, with a maximum relative aperture ratio 1:8, a maximum dispersion range < 0.04 mm at 230C/50V relative humidity and a temperature gradient of the focal length 6f mm
> 0.008
degree and
b) multi-lens objectives with at least one glass lens and 2 to 4 plastic lenses, with a maximum relative aperture ratio 1:5.6, maximum dispersion range < 0.04 mm at 23"C/50% relative humidity, and a temperature gradient of the focal length sf mm > 0.002 degree Because of their low speed, these objectives can only be used with favourable light conditions.
Furthermore, organic polymers are known which have a refractive index fld > 1.59, such as, for example, polycarbodiimides, polybenzimidazoles, polyvinylcarbazole and specific polycarbonates. These products cannot be employed for optical instruments because they are either coloured themselves or cannot be processed thermoplastically or cannot be prepared in a high-molecular weight form.
The polycarbonates for use according to the invention tend not to have these deficiencies, so that optical systems can be manufactured from them which have significant advantages compared with the state of the art. Examples of these advantages are:
1. Better correctability of the image formation errors with larger radii for the lens surfaces (making manufacture easier).
2. Increase in the relative aperture ratio with unchanged dispersion range.
3. Improved resolution by reducing the dispersion range with an unchanged relative aperture ratio.
4. Reduction of the temperature gradients in objectives furnished only with plastic lenses and in objectives furnished with glass lenses and plastic lenses.
5. Manufacture of lens systems with relative aperture ratios above 1:8 consisting only of plastic lenses.
Polycarbonates which are suitable for making lenses according to the invention are those consisting of 15-100 mol V of structural units of the formula
and 85-0 mol V of structural units of the formula
wherein
R denotes
R' denotes -H, -CIl3 or -Br, Those in which the structural unit II corresponds to the formula
are preferred and those which are built up from 35-50 mol V of structural units I and 65-50 mol V of structural units II are particularly preferred.
These polycarbonates fulfil the mechanical and thermal requirements placed on an optical material. They can be processed thermoplastically without impairing the mechanical and optical properties. They retain their shape under the influence of heat up to at least 900 C, possess a good impact strength, low shrinkage during processing, low coefficient of expansion, low weight, low absorption of water, good flow behaviour, good mould-release properties, good resistance to ageing and a colour triplet of 5.1; 0.1; 0, calculated according to DIN 4,522 part 5. Stabilisers,
UV absorbers, mould-releasing agents and antistatic agents can be incorporated without impairing these properties.
The polycarbonates can be prepared by known processes; for example by the melt trans-esterification process from bisphenol and diphenyl carbonate, and the two phase boundary process from bisphenols and phosgene.
The melt trans-esterification process is preferably used for polycarbonates with more than 50 mol V of structural units I because they are sparingly soluble.
Otherwise, the two phase boundary process, which is briefly described in the following, is preferred.
The bisphenols are dissolved in aqueous alkali, preferably in sodium hydroxide solution or potassium hydroxide solution, and a solvent which is suitable for the polycarbonate formed is added. Suitable solvents are, in general, chlorohydrocarbons, such as methylene chloride, chloroform and 1,2dichloroethane, but also chlorinated aromatic compounds, such as chlorobenzene, dichlorobenzene and chlorotoluene. Phosgene is passed into this mixture, whilst stirring vigorously.
In the case of bisphenols which, because of their hydrophobic character, give no bisphenolate solutions, a suspension is advantageously used.
The phosgenation required depends on the bisphenol employed, the stirring effect and the reaction temperature, which can be between about 10 and about 60"C, and in general is 1.1 to 3.0 mols of phosgene per mol of bisphenol.
After the phosgenation, which can also already be carried out in the presence of chain stoppers, for example phenol or substituted monophenols, the condensation reaction to give a high-molecular polycarbonate is then carried out by adding a tertiary amine, for example triethylamine, dimethylbenzylamine or triethylenediamine, as a catalyst. In general, the amounts of amine are 1 to 10 mol V relative to bisphenol, but 2 to 10 mol V are preferably used; in general, a reaction time of about 0.5 to about 1.5 hours is sufficient.
The polycarbonates can be branched by incorporating small amounts, preferably amounts between 0.05 and 2.0 mol V (relative to diphenols employed), of compounds which are tri-functional or more than tri-functional, in particular those with three or more than three phenolic hydroxyl groups.
The polycarbonates thus prepared can be isolated by known processes, for example by separating off the aqueous phase, washing the organic phase several times with water until free from electrolyte and thereafter precipitating the polycarbonate or evaporating off the solvent. The polycarbonates thus obtained contain no portions of saponifiable chlorine.
The yields are virtually quantitative.
Another preparation process is polycondensation in a homogeneous phase. In this process, the hydroxy compounds to be used are dissolved in an inert solvent, such as, for example, methylene chloride, with the addition of an equivalent amount of a tertiary base, such as, for example, N,N-dimethylaniline, dimethylcyclohexylamine or, preferably, pyridine. The polycondensation reaction is then carried out by passing in gaseous derivatives of carbonic acid or by adding solutions of liquid or solid derivatives of carbonic acid dropwise.
The chlorocarbonic acid esters of monovalent or more than divalent phenols can also be used in the processes described.
As mentioned above, it is also possible to obtain the polycarbonates for use in the invention by trans-esterification according to the melt polycondensation process.
For this, the bisphenols are advantageously reacted with diphenylcarbonate under an inert gas atmosphere in the presence of alkaline catalysts, such as, for example, oxides, hydroxides, carbonates, hydrides and phenolates of alkali metals and alkaline earth metals, at temperatures rising from 200 to 3600 C, preferably 240 to 3000C and under a pressure which is gradually reduced to 20-1 mm Hg and the phenol liberated during the reaction is continuously distilled off. The polymer formed is directly extruded and granulated.
A considerable advantage of the polycarbonates used in the invention is that the refractive index and optical dispersion of the materials can be determined freely, within certain limits. by the nature and amount of the co-condensed comonomers. New possibilites in the calculation and realisation of optical systems are thereby opened up.
Optical lenses can be manufactured from the polycarbonates in the customary manner by injection moulding. The resulting injection-moulded articles can be employed without further processing. The polycarbonates are essentially used for the manufacture of lenses and lens systems for cameras.
Example 1
Copolycarbonate of bisphenol A and bisphenol S xt 40.0 g (1 mol) of NaOH are dissolved in 600 ml of water, and 39.8 g (0.17 mol) of bisphenol A, 6.54 g (0.03 mol) of bisphenol S, 1.02 g (0.0068 mol) of p-tert.butylphenol and 600 ml of CH2Cl2 are then added, whilst stirring. 29.7 g (0.3 mol) of phosgene are passed in, whilst stirring vigorously. 2 ml of a 3V strength triethylamine solution are then added and the mixture is stirred vigorously for a further 90 minutes. The entire reaction is carried out under nitrogen and at 20 to 25"C. After the further stirring, the mixture is worked up. The aqueous phase is free from bisphenol. The organic phase is diluted with 1,000 ml of CH2CI2 and washed with 100 ml of 20% strength aqueous phosphoric acid and then with water until free from electrolyte. After concentrating the organic phase to 600 ml, this is added dropwise to 2,500 ml of methanol, whereupqn the polycarbonate precipitates. It is dried. The yield of white, flocculent polycarbonate is 44 g. The relative viscosity of the polycarbonate is 1.278 (in CH2CI2 at 250C, C=5 g/l).
Colourless, clear tough films can be drawn from the methylene chloride solution of the polymer. The optical data, measured on a film, are: n,=1.5929 vd=28.9.
x) 4,4'-dihydroxydiphenyl sulphide; 4,4'-thiodiphenol.
Example 2
Copolycarbonate of bisphenol A and bisphenol S
The procedure followed is according to Example 1 and, with a molar ratio of bisphenol A: bisphenol S=50:50, a colourless product with a relative viscosity 17rev of 1.282 (in CH2Cl2 at 25"C C=5 girl) is obtained. The optical data measured on a film are: no=1.6148 vd=25.6.
Example 3
Copolycarbonate of bisphenol A and bisphenol S x} 2,500 g (62.5 mols of NaOH are dissolved in 35 1 of water, and 1,710 g (7.5 mols) of bisphenol A, 1,090 g (5.0 mols) of bisphenol S. 75.11 g (0.5 mol) of p-tert.butylphenol and 2 g of NaB H4 are added to the solution, whilst stirring. After adding 351 of CH2CI2, 1,732 g (17.5 mols) of phosgene are passed in at 20 to 250C.
12.1 g of triethylamine are then added and the mixture is stirred for a further 60 minutes. The organic phase is washed twice with 2V strength phosphoric acid and then with water until free from electrolyte. The methylene chloride is evaporated off. The resulting polymer is comminuted, and dried for 48 hours in vacuo at 120"C. 2,630 g of a colourless product with a relative viscosity 71rev of 1.245 (in
CH2CI2, 25"C, C=5 girl) and a glass transition temperature of 132"C is obtained.
After adding 0.5V by weight of a UV absorber, the material is extruded at 2700 C.
The colourless granules are processed to injection-moulded articles; optical data; n,-1.61289; vd=26. I .
Example 4
Polycarbonate of bisphenol S x} 87.2 g (0.4 mol) of bisphenol S are mixed with 94.1 g (0.44 mol) of diphenylcarbonate, and 25 mg of a mixture of sodium bisphenolate and bisphenol
A (1:99) are added as the catalyst. The mixture is heated, whilst stirring. In the course of 5 hours, the temperature is increased from 220"C to 3000C and the pressure is reduced to a final value of I mm Hg. During this procedure, the phenol liberated distils off. After cooling the melt, the resulting polycarbonate is comminuted and moulded into test pieces by Injection. Optical data: no=1.6577; vd=22. 1.
x) 4,4'-dihydroxydiphenylsulphide; 4,4'-thiodiphenol.
Example 5
Copolycarbonate of bisphenol S x} and 4,4'-dihydroxytetraphenylmethane
The procedure followed is according to Example 1 and, with a ratio of 60 mol V of 4,4'-dihydroxytetraphenylmethane and 40 mol V of bisphenol S, 30 g of a colourless product with a relative viscosity of 1.224 (in CH2CI2 at 250C, C=5 girl) are obtained. The optical data, measured on a film, are: nd=1.63677; vd=25.4.
x) 4,4'-dihydroxydiphenyl sulphide, 4,4'-thiodiphenol.
EXAMPLE 6
The radii changes of a 3 lens objective were calculated using the optical data of the material from Example 4. It was assumed that a version exists as substantially shown and described in the drawing comprised of a glass lens (LaF2), a lens of bisphenol A-polycarbonate and a lens of PMMA (polymethyl-methacrylate) of the following values: Lens Material nd vd Vd L, LaF2 1.7440 44.77
L2 PC of bisphenol-A 1.5858 30.0
L3 PMMA 1.491 58.0
The measurements for lens 2 are:
L2 r3=-32.478 r4= +6.287
d2= 0.860
When replacing the lens of polycarbonate (lens 2) with the material used in
Example 4, the following measurements result:
L2, r13=-36.462 r'4= +7.058
d'2= 0.899
All other measurements of lenses 1 and 3 as well as the air distance 11 and 12 remained unchanged.
The focal distance of f=26.8 mm, the relative opening of 1:6.45, and the quality requirements (circle of divergence < 0.02 mm near the axis) remained unchanged.
WHAT WE CLAIM IS:
1. Optical lenses made from an aromatic polycarbonate with a relative viscosity free of 1.20 to 1.60 (measured in CH2Cl2 at 250C) consisting of 15-100 mol V of structural units of the formula
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (9)
1. Optical lenses made from an aromatic polycarbonate with a relative viscosity free of 1.20 to 1.60 (measured in CH2Cl2 at 250C) consisting of 15-100 mol V of structural units of the formula
and 854 mol V of structural units of the formula
wherein
R denotes
R' denotes -H, CH3 or -Br.
2. Lenses according to claim 1 wherein R is
and R' is -H.
3. Lenses according to claim I or 2 wherein the polycarbonate consists of 3550 mol V of structural units I and 65-50 mol V of structural units 11.
4. Lenses according to any one of claims 1 to 3 wherein the polycarbonate includes a stabiliser, U.V. absorber, mould release agent or anti-static agent.
5. Lenses according to any one of claims 1 to 4 wherein the polycarbonate is prepared by a melt trans-esterification process from a bisphenol and diphenyl carbonate, or by a two phase boundary process from a bisphenol and phosgene.
6. Lenses according to any one of claims 1 to 4 wherein the polycarbonate is prepared by polycondensation in a homogeneous phase.
7. Lenses according to any one of claims 1 to 6, for cameras.
8. An aromatic polycarbonate, when used for making optical lenses as defined in claim 1, substantially as hereinbefore described in any of Examples I to 5.
9. Optical lenses as claimed in claim I, substantially as hereinbefore described in Example 6 and with reference to the accompanying drawing.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2701173A DE2701173C2 (en) | 1977-01-13 | 1977-01-13 | Use of polycarbonates to manufacture lenses for photo and film cameras |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1592724A true GB1592724A (en) | 1981-07-08 |
Family
ID=5998590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB879/78A Expired GB1592724A (en) | 1977-01-13 | 1978-01-10 | Polycarbonate optical lenses |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5389752A (en) |
| DE (1) | DE2701173C2 (en) |
| FR (1) | FR2377267A1 (en) |
| GB (1) | GB1592724A (en) |
| IT (1) | IT1104626B (en) |
| NL (1) | NL186143C (en) |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2141556A (en) * | 1983-06-14 | 1984-12-19 | Pilkington Perkin Elmer Ltd | Glass and plastics objective lens for low light level viewing apparatus |
| US6180698B1 (en) | 1997-02-28 | 2001-01-30 | Candescent Technologies Corporation | Polycarbonate-containing liquid chemical formulation and method for making polycarbonate film |
| US6500885B1 (en) | 1997-02-28 | 2002-12-31 | Candescent Technologies Corporation | Polycarbonate-containing liquid chemical formulation and methods for making and using polycarbonate film |
| US7169333B2 (en) | 2000-05-12 | 2007-01-30 | Bayer Aktiengesellschaft | Antistatic agent |
| US7425358B2 (en) | 2004-05-07 | 2008-09-16 | Bayer Materialscience Ag | Copolycarbonates having improved flowability |
| US7847051B2 (en) | 2008-03-05 | 2010-12-07 | Bayer Materialscience Ag | Phase boundary processes for preparing polycarbonates |
| US7879967B2 (en) | 2007-04-03 | 2011-02-01 | Bayer Materialscience Ag | Modified polycarbonates, polyester carbonates and polyesters having improved elongation behavior and flame resistance |
| US7968671B2 (en) | 2008-05-15 | 2011-06-28 | Bayer Material Science Ag | Alkylphenol-terminated copolycarbonates, processes for preparing the same, molding compositions containing the same, and articles prepared therefrom |
| CN102272196A (en) * | 2008-12-31 | 2011-12-07 | 沙伯基础创新塑料知识产权有限公司 | Camera lenses prepared from thermoplastic compositions having high flow and ductility, and method of preparing camera lenses |
| US8110649B2 (en) | 2008-02-29 | 2012-02-07 | Bayer Materialscience Ag | Polycarbonates comprising cyclic oligomers and having an improved flow behavior |
| US8158745B2 (en) | 2008-04-18 | 2012-04-17 | Bayer Materialscience Ag | Polycarbonates having rearrangement structures, cyclic and linear oligomers and also flow behavior |
| US8202961B2 (en) | 2008-02-13 | 2012-06-19 | Bayer Materialscience Ag | Alkylphenol for adjusting the molecular weight, and polycarbonate compositions having improved properties |
| US8329852B2 (en) | 2008-11-28 | 2012-12-11 | Bayer Materialscience Ag | Copolycarbonates having improved surface hardness |
| US8507635B2 (en) | 2008-08-05 | 2013-08-13 | Bayer Intellectual Property Gmbh | Modified polycarbonates having improved surface properties |
| US9139730B2 (en) | 2009-03-26 | 2015-09-22 | Bayer Materialscience Ag | (Co)polycarbonates with improved optical properties |
| US9771451B2 (en) | 2014-01-24 | 2017-09-26 | Covestro Deutschland Ag | Method for producing polycarbonate according to the phase interface method |
| US11319398B2 (en) | 2017-02-02 | 2022-05-03 | Covestro Deutschland Ag | Method for the production of polyoxazolidinone polymer compounds |
| US11326018B2 (en) | 2016-08-19 | 2022-05-10 | Covestro Deutschland Ag | Process for the synthesis of polyoxazolidinone compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5778419A (en) * | 1977-09-06 | 1982-05-17 | Mobay Chemical Corp | Copolycarbonate |
| EP0084578A1 (en) * | 1982-01-23 | 1983-08-03 | Mobay Chemical Corporation | Copolycarbonates having high melt flow rates |
| JPS58179224A (en) * | 1982-03-18 | 1983-10-20 | Konishiroku Photo Ind Co Ltd | Optical resin composition and optical element |
| JPS59115333A (en) * | 1982-12-22 | 1984-07-03 | Toshiba Corp | Production of polysulfide carbonate |
| JPS617314A (en) * | 1984-06-20 | 1986-01-14 | Kureha Chem Ind Co Ltd | Lens material having high refractive index |
| JPH0649750B2 (en) * | 1984-08-24 | 1994-06-29 | 三菱化成株式会社 | Injection molding material consisting of polycarbonate |
| JPH0662752B2 (en) * | 1984-08-24 | 1994-08-17 | 三菱化成株式会社 | Optical information material |
| JPH0792542B2 (en) * | 1986-02-07 | 1995-10-09 | ミノルタ株式会社 | Triplet lens system after diaphragm |
| US4831110A (en) * | 1986-12-19 | 1989-05-16 | Daicel Chemical Industries, Ltd. | Co-polycarbonate copolymer from 2,2-bis(4-hydroxy-3-tertiary butyl phenyl)propane and optical disk |
| US5486949A (en) | 1989-06-20 | 1996-01-23 | The Dow Chemical Company | Birefringent interference polarizer |
| EP0500129B1 (en) * | 1991-02-22 | 1996-07-31 | Mitsubishi Gas Chemical Company, Inc. | Polycarbonate resin solution for film formation by casting |
| EP0500128B1 (en) * | 1991-02-22 | 1998-06-10 | Mitsubishi Gas Chemical Company, Inc. | Polycarbonate resin solution for film formation by casting |
| JPH07509269A (en) * | 1992-07-16 | 1995-10-12 | ザ・ダウ・ケミカル・カンパニー | Thiodiphenol copolycarbonates and their use as components of multilayer polymeric reflective objects |
| US5532331A (en) * | 1993-06-24 | 1996-07-02 | The Dow Chemical Company | Thiodiphenol copolycarbonates and their use as components of multilayered polymeric reflective bodies |
| JP2002114842A (en) * | 2000-10-06 | 2002-04-16 | Mitsui Chemicals Inc | Polycarbonate resin and optical part composed by including the same |
| JP2002114841A (en) * | 2000-10-06 | 2002-04-16 | Mitsui Chemicals Inc | Optical part |
| DE102007040925A1 (en) | 2007-08-30 | 2009-03-05 | Bayer Materialscience Ag | Thermoplastic compositions with low haze |
| DE102008008841A1 (en) | 2008-02-13 | 2009-08-20 | Bayer Materialscience Ag | Preparing (co)polycarbonate or diaryl carbonate, useful in e.g. sunglasses, comprises converting di-, mono-phenol and phosgene to chloroformic acid aryl ester, oligo- or diaryl-carbonate, and reacting the product under alkaline solution |
| EP2090605B1 (en) | 2008-02-13 | 2011-07-13 | Bayer MaterialScience AG | Method for making polycarbonates |
| US8064140B2 (en) | 2008-12-31 | 2011-11-22 | Sabic Innovative Plastics Ip B.V. | Transparent articles prepared from thermoplastic compositions having low birefringence |
| DE102009013643A1 (en) | 2009-03-18 | 2010-09-30 | Bayer Materialscience Ag | Copolycarbonates with improved properties |
| EP2336245A1 (en) | 2009-12-12 | 2011-06-22 | Bayer MaterialScience AG | Polycarbonate compounds with improved surface hardness |
| DE102009058099A1 (en) | 2009-12-12 | 2011-06-16 | Bayer Materialscience Ag | Polycarbonate blends with high heat resistance and improved surface properties |
| DE102009058462A1 (en) | 2009-12-16 | 2011-06-22 | Bayer MaterialScience AG, 51373 | Producing polycarbonate injection molded body comprises introducing injection molded bodies containing polycarbonate in reactor, inerting atmosphere of reactor, introducing fluorine-inert gas mixture and evacuating and flushing the reactor |
| JP6860806B2 (en) * | 2016-05-27 | 2021-04-21 | 三菱瓦斯化学株式会社 | Polycarbonate resin for optics |
| EP3985047A1 (en) | 2020-10-13 | 2022-04-20 | Covestro Deutschland AG | Method for the preparation of a polycarbonate based on the interfacial process with solvent exchange |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL111669C (en) * | 1955-04-14 | |||
| US3250744A (en) * | 1956-10-19 | 1966-05-10 | Bayer Ag | High molecular weight thermoplastic polycarbonates and process for the production thereof |
| US4043980A (en) * | 1976-05-18 | 1977-08-23 | Mobay Chemical Corporation | Flame retardant polycarbonate having improved critical thickness |
-
1977
- 1977-01-13 DE DE2701173A patent/DE2701173C2/en not_active Expired
-
1978
- 1978-01-10 GB GB879/78A patent/GB1592724A/en not_active Expired
- 1978-01-10 NL NLAANVRAGE7800292,A patent/NL186143C/en not_active IP Right Cessation
- 1978-01-11 IT IT47588/78A patent/IT1104626B/en active
- 1978-01-11 JP JP123078A patent/JPS5389752A/en active Pending
- 1978-01-13 FR FR7800977A patent/FR2377267A1/en active Granted
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2141556A (en) * | 1983-06-14 | 1984-12-19 | Pilkington Perkin Elmer Ltd | Glass and plastics objective lens for low light level viewing apparatus |
| US6180698B1 (en) | 1997-02-28 | 2001-01-30 | Candescent Technologies Corporation | Polycarbonate-containing liquid chemical formulation and method for making polycarbonate film |
| US6500885B1 (en) | 1997-02-28 | 2002-12-31 | Candescent Technologies Corporation | Polycarbonate-containing liquid chemical formulation and methods for making and using polycarbonate film |
| US7169333B2 (en) | 2000-05-12 | 2007-01-30 | Bayer Aktiengesellschaft | Antistatic agent |
| US7425358B2 (en) | 2004-05-07 | 2008-09-16 | Bayer Materialscience Ag | Copolycarbonates having improved flowability |
| US7879967B2 (en) | 2007-04-03 | 2011-02-01 | Bayer Materialscience Ag | Modified polycarbonates, polyester carbonates and polyesters having improved elongation behavior and flame resistance |
| US8202961B2 (en) | 2008-02-13 | 2012-06-19 | Bayer Materialscience Ag | Alkylphenol for adjusting the molecular weight, and polycarbonate compositions having improved properties |
| US8110649B2 (en) | 2008-02-29 | 2012-02-07 | Bayer Materialscience Ag | Polycarbonates comprising cyclic oligomers and having an improved flow behavior |
| US7847051B2 (en) | 2008-03-05 | 2010-12-07 | Bayer Materialscience Ag | Phase boundary processes for preparing polycarbonates |
| US8158745B2 (en) | 2008-04-18 | 2012-04-17 | Bayer Materialscience Ag | Polycarbonates having rearrangement structures, cyclic and linear oligomers and also flow behavior |
| US7968671B2 (en) | 2008-05-15 | 2011-06-28 | Bayer Material Science Ag | Alkylphenol-terminated copolycarbonates, processes for preparing the same, molding compositions containing the same, and articles prepared therefrom |
| US8507635B2 (en) | 2008-08-05 | 2013-08-13 | Bayer Intellectual Property Gmbh | Modified polycarbonates having improved surface properties |
| US8329852B2 (en) | 2008-11-28 | 2012-12-11 | Bayer Materialscience Ag | Copolycarbonates having improved surface hardness |
| CN102272196A (en) * | 2008-12-31 | 2011-12-07 | 沙伯基础创新塑料知识产权有限公司 | Camera lenses prepared from thermoplastic compositions having high flow and ductility, and method of preparing camera lenses |
| CN102272196B (en) * | 2008-12-31 | 2014-05-21 | 沙伯基础创新塑料知识产权有限公司 | Camera lenses prepared from thermoplastic compositions having high flow and ductility, and method of preparing camera lenses |
| US9139730B2 (en) | 2009-03-26 | 2015-09-22 | Bayer Materialscience Ag | (Co)polycarbonates with improved optical properties |
| US9771451B2 (en) | 2014-01-24 | 2017-09-26 | Covestro Deutschland Ag | Method for producing polycarbonate according to the phase interface method |
| US11326018B2 (en) | 2016-08-19 | 2022-05-10 | Covestro Deutschland Ag | Process for the synthesis of polyoxazolidinone compounds |
| US11319398B2 (en) | 2017-02-02 | 2022-05-03 | Covestro Deutschland Ag | Method for the production of polyoxazolidinone polymer compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5389752A (en) | 1978-08-07 |
| FR2377267A1 (en) | 1978-08-11 |
| FR2377267B1 (en) | 1983-07-01 |
| NL186143C (en) | 1990-10-01 |
| NL186143B (en) | 1990-05-01 |
| IT7847588A0 (en) | 1978-01-11 |
| IT1104626B (en) | 1985-10-21 |
| NL7800292A (en) | 1978-07-17 |
| DE2701173C2 (en) | 1983-02-10 |
| DE2701173A1 (en) | 1978-07-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |