WO2000024805A1 - Processable polycarbonates containing alkyl carbonate end groups - Google Patents
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- WO2000024805A1 WO2000024805A1 PCT/US1999/014335 US9914335W WO0024805A1 WO 2000024805 A1 WO2000024805 A1 WO 2000024805A1 US 9914335 W US9914335 W US 9914335W WO 0024805 A1 WO0024805 A1 WO 0024805A1
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- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
- G11B7/2533—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
- G11B7/2534—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins polycarbonates [PC]
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- 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
- C08G64/14—Aromatic polycarbonates not containing aliphatic unsaturation containing a chain-terminating or -crosslinking agent
Definitions
- This invention relates to polycarbonates, and more particularly to aromatic polycarbonates of improved processability.
- Aromatic polycarbonates are a well known class of engineering thermoplastics, valuable by reason of such advantageous properties as high impact resistance and transparency. They are useful in many diverse applications, including the fabrication of optical recording media such as optical disks.
- a convenient method for synthesizing such polycarbonates is the so-called "interfacial" method, performed in a mixture of water and a water-immiscible organic liquid. It comprises the reaction of at least one dihydroxyaromatic compound with a carbonyl halide such as phosgene, under alkaline conditions and in the presence of an interfacial polycarbonate formation catalyst.
- the reaction may be essentially a one-step reaction or may proceed via initial formation of an oligomeric chloroformate; i.e., a monochloroformate or bischloroformate.
- the molecular weight of the polycarbonate product may be regulated by incorporating in the reaction mixture at least one monohydroxyaromatic compound as a chain termination agent, whereupon the polycarbonate has end groups derived from said monohydroxyaromatic compound.
- the present invention is based on the discovery that aromatic polycarbonates having relatively long chain alkyl end groups can be prepared interfacially via chloroformate intermediates. Such polycarbonates are highly processable, even when they contain birefringence-reducing units.
- the invention includes aromatic polycarbonates having end groups of the formula
- R 1 is a primary or secondary alkyl radical containing at least 3 carbon atoms.
- Another aspect of the invention is a method for preparing such aromatic polycarbonates which comprises contacting a two-phase mixture comprising water, at least one dihydroxyaromatic compound, at least one chloroformate of the formula R'OCOCl wherein R 1 is as previously defined, at least one alkali metal hydroxide, at least one interfacial polycarbonate formation catalyst and a substantially inert, substantially water-insoluble organic liquid with at least one carbonyl halide.
- optical recording media comprising polycarbonates of the type defined hereinabove.
- the polycarbonates of the present invention are conventional polymers. Thus, they may be characterized as comprising structural groups having one or more structures of the formula
- a 1 is a divalent aromatic radical which may be an aromatic hydrocarbon or a substituted aromatic hydrocarbon radical, with illustrative substituents being alkyl, cycloaikyl, alkenyl (e.g., crosslinkable-graftable moieties such as allyl), halo (especially fluoro, chloro and/or bromo), nitro and alkoxy.
- the preferred A 1 values have the formula
- each of A 2 and A 3 is a monocyclic divalent aromatic radical and Y is a single bond or a bridging radical in which one or two atoms separate A 2 from A 3 .
- the free valence bonds in formula II are usually in the meta or para positions of A 2 and A 3 in relation to Y.
- the A2 and A3 values may be unsubsti- tuted phenylene or substituted derivatives thereof wherein the substituents are as defined for Al.
- Unsubstituted phenylene radicals are preferred, but it is also contemplated to employ, for example, polymers in which each of A2 and A3 has two methyl substituents in ortho positions to the free valence bond.
- Both A2 and A3 are preferably p-phenylene, although both may be o- or m-phenylene or one o- or m-phenylene and the other p-phenylene.
- the bridging radical, Y is one in which one or two atoms, preferably one, separate A2 from A3. It is most often a hydrocarbon radical and particularly a saturated Cl-12 aliphatic or alicyclic radical.
- Illustrative radicals are methylene, cyclohexylmethylene, [2.2.1]bicycloheptyl-methylene, ethylene, ethylidene, 2,2-propylidene, l, l-(2,2-dimethyl-propylidene), phenylethylidene, cyclohexylidene,
- Aryl-substituted radicals are included, as are unsaturated radicals and radicals containing atoms other than carbon and hydrogen; e.g., oxy groups. Substituents such as those previously enumerated may be present on the aliphatic, alicyclic and aromatic portions of the Y group.
- the preferred units containing moieties of formula III are those in which each of A2 and A3 is p-phenylene and Y is isopropylidene; i.e., those derived from bisphenol A.
- R 2 is C,. 4 alkyl and n is 0 or 1.
- n is 0; i.e., SBI units.
- the units of formula II usually comprise about 75-85 mole percent of such copolycarbonates, with units of formula V or, preferably, IV comprising the remaining 15-25 mole percent.
- An essential feature of the polycarbonates of the invention is the presence of end groups of formula I. These end groups are linked to the polycarbonate molecule via carbonate groups; i.e., the moieties of formula I are linked through oxygen to the aromatic radicals therein.
- the R 1 values in said end groups are primary or secondary, preferably primary, alkyl radicals having at least 3, preferably about 4-30 and most preferably about 10-20 carbon atoms.
- Illustrative radicals of this type are n-butyl, n-octyl, n-decyl, n- dodecyl and n-octadecyl.
- polycarbonates are prepared by an interfacial reaction which is, in many ways, conventional. It employs one or more dihydroxyaromatic compounds (hereinafter sometimes "bisphenols" for brevity) corresponding to the structural units desired in the polymeric product. It is, however, novel in that at least one chloroformate corresponding to the desired polymer end groups is incorporated in the reaction mixture as a chain termination agent. Many of such chloroformates are comrnercially available, or they may be prepared by phosgenation of the corresponding alcohol under anhydrous conditions.
- dihydroxyaromatic compounds hereinafter sometimes "bisphenols" for brevity
- the method may be conducted batchwise or continuously.
- Carbonyl halide usually phosgene, is most often employed in a molar ratio to bisphenol(s) in the range of about 1.1- 1.5: 1.
- Alkali metal hydroxide most often sodium hydroxide, is introduced so as to provide a pH within the range of about 9-12, preferably about 10- 11.
- the proportion of chain termination agent employed will depend on the molecular weight desired in the product polycarbonate; for the most part, it will be in the range of about 1-10 mole percent based on bisphenol.
- Interfacial polycarbonate formation catalysts which may be employed in the method of the invention include trialkyla ines and analogous heterocyclic amines such as triethylamine and 4-dtaethylam omorpholine and phase transfer catalysts.
- the latter include quaternary ammonium and quaternary phosphonium salts such as tetra-n-butylamrnonium bromide and tetraethylphosphonium bromide and hexaall ⁇ lguanidiniurn salts such as hexaethylguanidinium chloride.
- Such catalysts are typically employed in the amount of about 0.001-0.01 mole percent based on bisphenol.
- the organic liquid should be substantially insoluble in water.
- Illustrative liquids are aliphatic hydrocarbons such as hexane and n-heptane; chlorinated aliphatic hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, trichloro- ethane, tetrachloroethane, dichloropropane and 1 ,2-dichloroethylene; aromatic hydrocarbons such as benzene, toluene and xylene; substituted aromatic hydrocarbons such as chlorobenzene, o- dichlorobenzene, the chlorotoluenes, nitrobenzene and acetophenone; and carbon disulfide.
- the chlorinated aliphatic hydrocarbons, especially methylene chloride are preferred.
- the volume ratio of said organic liquid to water in the reaction mixture is most often in the range of about 1.5-5.0: 1.
- a reaction mixture comprising the organic liquid, water, bisphenol(s), catalyst and chloroformate is adjusted to the desired pH by addition of alkali metal hydroxide, typically in aqueous solution at a concentration in the range of about 25-60%. Phosgene is then passed into the mixture at a temperature in the range of about 15- 50°C, most often under reflux.
- the desired polycarbonate is formed and may be isolated by conventional techniques, as illustrated by anti-solvent (e.g., methanol) precipitation and steam precipitation.
- optical information storage media of the invention include such articles as audio disks, laser disks, optical disk memories and magnetoooptical disks to which inforrnation may be written and from which it may be read by laser.
- Such media may be produced from the polycarbonates of the invention by art-recognized means.
- polycarbonates of this invention have, in general, properties smiilar or identical to similar polycarbonates having other end groups. They are, however, characterized by improved processability as demonstrated by decreased Tg values.
- a polycarbonate according to the invention prepared with the use of 4.5 mole percent chain termination agent will have a Tg at least 10°C lower than a similar polycarbonate prepared with the use of p-cumylphenol.
- a 500-ml Morton flask fitted with a reflux condenser, phosgene addition tube, stirring means and pH probe was charged with 3.8 g (12.3 mmol) of SBI, 11.5 g (50.4 mmol) of bisphenol A, 120 ml of methylene chloride, 50 ml of distilled water and 150 ⁇ l (1.08 ⁇ mol) of triethylamine.
- the pH of the mixture was adjusted to 10.5 by the addition of 33% (by weight) aqueous sodium hydroxide solution and 830 mg (2.8 mmol, 4.5 mole percent based on bisphenols) of octadecyl chloroformate was added, with vigorous stirring.
- Example 2 The procedure of Example 1 was repeated, substituting n- octyl chloroformate for the n-octadecyl chloroformate.
- the resulting polycarbonate had a Tg of 153°C .
- a bisphenol A homopolycarbonate was prepared by a procedure sirnilar to that of Example 1 , using n-butyl chloroformate as the chain termination agent.
- the resulting polycarbonate had a Tg of 140°C, as compared with 150°C for a similar polycarbonate prepared using p-cumylphenol as the chain termination agent.
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Abstract
Polycarbonates having primary or secondary alkyl end groups with at least 3 carbon atoms are prepared by interfacial methods, employing an alkyl chloroformate such as n-octadecyl chloroformate as a chain termination agent. They are characterized by lower glass transition temperatures than corresponding aryl-terminated polycarbonates, and are therefore more processable. In particular, those having structural units characteristic of optical grade polymers are more easily processed.
Description
PROCESSABLE POLYCARBONATES CONTAINING ALKYL CARBONATE END GROUPS
BACKGROUND OF THE INVENTION
This invention relates to polycarbonates, and more particularly to aromatic polycarbonates of improved processability.
Aromatic polycarbonates are a well known class of engineering thermoplastics, valuable by reason of such advantageous properties as high impact resistance and transparency. They are useful in many diverse applications, including the fabrication of optical recording media such as optical disks.
A convenient method for synthesizing such polycarbonates is the so-called "interfacial" method, performed in a mixture of water and a water-immiscible organic liquid. It comprises the reaction of at least one dihydroxyaromatic compound with a carbonyl halide such as phosgene, under alkaline conditions and in the presence of an interfacial polycarbonate formation catalyst. The reaction may be essentially a one-step reaction or may proceed via initial formation of an oligomeric chloroformate; i.e., a monochloroformate or bischloroformate. The molecular weight of the polycarbonate product may be regulated by incorporating in the reaction mixture at least one monohydroxyaromatic compound as a chain termination agent, whereupon the polycarbonate has end groups derived from said monohydroxyaromatic compound.
The recent development of consumer-recordable and rerecordable optical disks has necessitated the development of polycarbonates having very low birefringence values. One route to products of this kind is via the incorporation of structural units characterized by low birefringence, such as those derived from such
bisphenols as 2,2-bis(3,5-dimethyl-4-hydroxyphenyl)propane,
9,9-bis(4-hydroxyphenyl) fluorene, l, l-bis(4-hydroxyphenyl)
- 1-phenylethane, l, l-bis(4- hydroxyphenyl) 3,3,5-trimethyl- cyclohexane, spiro(bis)indanediols such as 6,6'-hydroxy-3,3,3',3' -tetramethyl- l, l '-spiro(bis)indane (hereinafter "SBI"), and hydroxyphenylindanols such as l , l,3-trirnethyl-3-(4- hydroxyphenyl) - 5-hydroxyindane. The presence of such units generally results in polycarbonates of very low birefringence, but it exacts a price in that said polycarbonates have higher glass transition temperatures (Tg) than conventional polycarbonates and are therefore more difficult to process.
Various methods for improving the processability of polycarbonates, particularly those containing birefringence-reducing units, have been disclosed. They include incorporation of aliphatic dicarboxylic acid ester units; e.g., dodecanedioate units, and of units derived from polyalkylene glycols. The first of these methods has the disadvantage of generating a number of by-product structural units containing anhydride moieties, which are relatively unstable. The second requires preparation of the polycarbonate by transesterification, since polymers containing polyoxyalkylene carbonate units cannot be prepared interfacially.
It is of interest, therefore, to develop polycarbonates having a high degree of processability which are capable of preparation by relatively simple synthetic procedures, especially interfacial procedures. It is also of interest to develop such polycarbonates which do not contain unstable moieties.
SUMMARY OF THE INVENTION
The present invention is based on the discovery that aromatic polycarbonates having relatively long chain alkyl end groups
can be prepared interfacially via chloroformate intermediates. Such polycarbonates are highly processable, even when they contain birefringence-reducing units.
In one of its aspects, the invention includes aromatic polycarbonates having end groups of the formula
(I) R10 C
wherein R1 is a primary or secondary alkyl radical containing at least 3 carbon atoms.
Another aspect of the invention is a method for preparing such aromatic polycarbonates which comprises contacting a two-phase mixture comprising water, at least one dihydroxyaromatic compound, at least one chloroformate of the formula R'OCOCl wherein R1 is as previously defined, at least one alkali metal hydroxide, at least one interfacial polycarbonate formation catalyst and a substantially inert, substantially water-insoluble organic liquid with at least one carbonyl halide.
Still another aspect is optical recording media comprising polycarbonates of the type defined hereinabove.
DETAILED DESCRIPTION; PREFERRED EMBODIMENTS
Except for the end groups thereon, the polycarbonates of the present invention are conventional polymers. Thus, they may be characterized as comprising structural groups having one or more structures of the formula
The preferred A1 values have the formula
(III) -A2-Y-A3- ,
wherein each of A2 and A3 is a monocyclic divalent aromatic radical and Y is a single bond or a bridging radical in which one or two atoms separate A2 from A3. The free valence bonds in formula II are usually in the meta or para positions of A2 and A3 in relation to Y.
In formula III, the A2 and A3 values may be unsubsti- tuted phenylene or substituted derivatives thereof wherein the substituents are as defined for Al. Unsubstituted phenylene radicals are preferred, but it is also contemplated to employ, for example, polymers in which each of A2 and A3 has two methyl substituents in ortho positions to the free valence bond. Both A2 and A3 are preferably p-phenylene, although both may be o- or m-phenylene or one o- or m-phenylene and the other p-phenylene.
The bridging radical, Y, is one in which one or two atoms, preferably one, separate A2 from A3. It is most often a hydrocarbon radical and particularly a saturated Cl-12 aliphatic or alicyclic radical. Illustrative radicals are methylene, cyclohexylmethylene, [2.2.1]bicycloheptyl-methylene, ethylene, ethylidene, 2,2-propylidene, l, l-(2,2-dimethyl-propylidene), phenylethylidene, cyclohexylidene,
3,3,5-trimethyl-cyclohexylidene, cyclopentadecylidene, cyclodo- decylidene, 9,9-fluorenylidene and 2,2-adamantylidene, especially an alkylidene radical. Aryl-substituted radicals are included, as are unsaturated radicals and radicals containing atoms other than
carbon and hydrogen; e.g., oxy groups. Substituents such as those previously enumerated may be present on the aliphatic, alicyclic and aromatic portions of the Y group.
For most purposes, the preferred units containing moieties of formula III are those in which each of A2 and A3 is p-phenylene and Y is isopropylidene; i.e., those derived from bisphenol A.
In the preferred polycarbonates of the invention and especially those to be used for the fabrication of optical recording media, at least a portion and most preferably only a portion of the structural units have one of the formulas
and
wherein R2 is C,.4 alkyl and n is 0 or 1. Most preferred are the units of formula TV in which n is 0; i.e., SBI units. The units of formula II usually comprise about 75-85 mole percent of such copolycarbonates,
with units of formula V or, preferably, IV comprising the remaining 15-25 mole percent.
An essential feature of the polycarbonates of the invention is the presence of end groups of formula I. These end groups are linked to the polycarbonate molecule via carbonate groups; i.e., the moieties of formula I are linked through oxygen to the aromatic radicals therein. The R1 values in said end groups are primary or secondary, preferably primary, alkyl radicals having at least 3, preferably about 4-30 and most preferably about 10-20 carbon atoms. Illustrative radicals of this type are n-butyl, n-octyl, n-decyl, n- dodecyl and n-octadecyl.
In accordance with the method of this invention, polycarbonates are prepared by an interfacial reaction which is, in many ways, conventional. It employs one or more dihydroxyaromatic compounds (hereinafter sometimes "bisphenols" for brevity) corresponding to the structural units desired in the polymeric product. It is, however, novel in that at least one chloroformate corresponding to the desired polymer end groups is incorporated in the reaction mixture as a chain termination agent. Many of such chloroformates are comrnercially available, or they may be prepared by phosgenation of the corresponding alcohol under anhydrous conditions.
The method may be conducted batchwise or continuously. Carbonyl halide, usually phosgene, is most often employed in a molar ratio to bisphenol(s) in the range of about 1.1- 1.5: 1. Alkali metal hydroxide, most often sodium hydroxide, is introduced so as to provide a pH within the range of about 9-12, preferably about 10- 11. The proportion of chain termination agent employed will depend on the molecular weight desired in the product
polycarbonate; for the most part, it will be in the range of about 1-10 mole percent based on bisphenol.
Interfacial polycarbonate formation catalysts which may be employed in the method of the invention include trialkyla ines and analogous heterocyclic amines such as triethylamine and 4-dtaethylam omorpholine and phase transfer catalysts. The latter include quaternary ammonium and quaternary phosphonium salts such as tetra-n-butylamrnonium bromide and tetraethylphosphonium bromide and hexaall^lguanidiniurn salts such as hexaethylguanidinium chloride. Such catalysts are typically employed in the amount of about 0.001-0.01 mole percent based on bisphenol.
The organic liquid should be substantially insoluble in water. Illustrative liquids are aliphatic hydrocarbons such as hexane and n-heptane; chlorinated aliphatic hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, trichloro- ethane, tetrachloroethane, dichloropropane and 1 ,2-dichloroethylene; aromatic hydrocarbons such as benzene, toluene and xylene; substituted aromatic hydrocarbons such as chlorobenzene, o- dichlorobenzene, the chlorotoluenes, nitrobenzene and acetophenone; and carbon disulfide. The chlorinated aliphatic hydrocarbons, especially methylene chloride, are preferred. The volume ratio of said organic liquid to water in the reaction mixture is most often in the range of about 1.5-5.0: 1.
According to a typical batch embodiment of the method of the invention, a reaction mixture comprising the organic liquid, water, bisphenol(s), catalyst and chloroformate is adjusted to the desired pH by addition of alkali metal hydroxide, typically in aqueous solution at a concentration in the range of about 25-60%. Phosgene is then passed into the mixture at a temperature in the range of about 15- 50°C, most often under reflux. The desired polycarbonate is formed
and may be isolated by conventional techniques, as illustrated by anti-solvent (e.g., methanol) precipitation and steam precipitation.
The optical information storage media of the invention include such articles as audio disks, laser disks, optical disk memories and magnetoooptical disks to which inforrnation may be written and from which it may be read by laser. Such media may be produced from the polycarbonates of the invention by art-recognized means.
The polycarbonates of this invention have, in general, properties smiilar or identical to similar polycarbonates having other end groups. They are, however, characterized by improved processability as demonstrated by decreased Tg values. For the most part, a polycarbonate according to the invention prepared with the use of 4.5 mole percent chain termination agent will have a Tg at least 10°C lower than a similar polycarbonate prepared with the use of p-cumylphenol.
The invention is illustrated by the following examples.
EXAMPLE 1
A 500-ml Morton flask fitted with a reflux condenser, phosgene addition tube, stirring means and pH probe was charged with 3.8 g (12.3 mmol) of SBI, 11.5 g (50.4 mmol) of bisphenol A, 120 ml of methylene chloride, 50 ml of distilled water and 150 μl (1.08 μmol) of triethylamine. The pH of the mixture was adjusted to 10.5 by the addition of 33% (by weight) aqueous sodium hydroxide solution and 830 mg (2.8 mmol, 4.5 mole percent based on bisphenols) of octadecyl chloroformate was added, with vigorous stirring. Phosgene, 7.6 g (76 mmol), was added over about 30 minutes as stirring was continued, with maintenance of the pH at 10.5 by addition of aqueous
sodium hydroxide solution as necessary. When polymerization was complete, the organic phase was separated and the desired polycarbonate was isolated therefrom by precipitation into boiling water. Its weight average molecular weight, as determined by gel permeation chromatography, was 38,800. Its Tg was 143°C, as compared with 163°C for a sirnilar polycarbonate having p- cumylphenol- derived end groups.
EXAMPLE 2
The procedure of Example 1 was repeated, substituting n- octyl chloroformate for the n-octadecyl chloroformate. The resulting polycarbonate had a Tg of 153°C .
EXAMPLE 3
A bisphenol A homopolycarbonate was prepared by a procedure sirnilar to that of Example 1 , using n-butyl chloroformate as the chain termination agent. The resulting polycarbonate had a Tg of 140°C, as compared with 150°C for a similar polycarbonate prepared using p-cumylphenol as the chain termination agent.
Claims
1. An aromatic polycarbonate having end groups of the formula
O
(I) R10 C
wherein R1 is a primary or secondary alkyl radical containing at least 3 carbon atoms.
2. A polycarbonate according to claim 1 which comprises structural units having one or more structures of the formula
wherein A1 is a divalent aromatic radical.
3. A polycarbonate according to claim 2 which is a bisphenol A homopolycarbonate.
4. A polycarbonate according to claim 2 which is a copolycarbonate of bisphenol A and 6,6'-hydroxy-3,3,3',3'-tetra- methyl- l , l'-spiro(bis)indane.
5. A polycarbonate according to claim 2 wherein Rl is a primary alkyl radical having about 4-30 carbon atoms.
6. A polycarbonate according to claim 5 wherein Rl is n-butyl.
7. A polycarbonate according to claim 5 wherein Rl is n-octyl.
8. A polycarbonate according to claim 5 wherein Rl is n-octadecyl.
9. A method for preparing an aromatic polycarbonate which comprises contacting a two-phase mixture comprising water, at least one dihydroxyaromatic compound, at least one chloroformate of the formula RlOCOCl wherein Rl is a primary or secondary alkyl radical containing at least 3 carbon atoms, at least one alkali metal hydroxide, at least one interfacial polycarbonate formation catalyst and a substantially inert, substantially water-insoluble organic liquid with at least one carbonyl halide.
10. A method according to claim 9 wherein the organic liquid is methylene chloride.
11. A method according to claim 9 wherein the alkali metal hydroxide is sodium hydroxide.
12. method according to claim 9 wherein the carbonyl halide is phosgene.
13. method according to claim 9 wherein the temperature is in the range of about 15-50°C.
14. method according to claim 9 wherein the dihydroxyaromatic compound is bisphenol A.
15. method according to claim 9 wherein the dihydroxyaromatic compound is a mixture of bisphenol A and 6,6'-hydroxy-3,3,3',3'-tetramethyl- 1 , 1 '-spiro(bis)indane.
16. method according to claim 9 wherein Rl is a primary alkyl radical having about 4-30 carbon atoms.
17. method according to claim 9 wherein Rl is n-butyl.
18. method according to claim 9 wherein Rl is n-octyl.
19. method according to claim 9 wherein Rl is n-octadecyl.
20. n optical recording medium comprising an aromatic polycarbonate having end groups of the formula
wherein R1 is a primary or secondary alkyl radical containing at least 3 carbon atoms.
21. n aromatic polycarbonate having end groups of the formula
where R1 is n-butyl, n-octyl or n-octadecyl, and the polycarbonate is a bisphenol A homopoly carbonate.
22. n optical recording medium comprising an aromatic polycarbonate having end groups of the formula
(I) R10 C
where R1 is n-butyl, n-octyl or n-octyl, or n-octadecyl and the polycarbonate is a bisphenol A homopolycarbonate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17875698A | 1998-10-26 | 1998-10-26 | |
| US09/178,756 | 1998-10-26 |
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| WO2000024805A1 true WO2000024805A1 (en) | 2000-05-04 |
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| DATABASE WPI Week 8547, Derwent World Patents Index; AN 1985-293936, XP002117912 * |
| PATENT ABSTRACTS OF JAPAN vol. 199, no. 810 31 August 1998 (1998-08-31) * |
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