EP0000396B1 - Verfahren zur Herstellung von flammhemmenden Polycarbonaten - Google Patents
Verfahren zur Herstellung von flammhemmenden Polycarbonaten Download PDFInfo
- Publication number
- EP0000396B1 EP0000396B1 EP78100379A EP78100379A EP0000396B1 EP 0000396 B1 EP0000396 B1 EP 0000396B1 EP 78100379 A EP78100379 A EP 78100379A EP 78100379 A EP78100379 A EP 78100379A EP 0000396 B1 EP0000396 B1 EP 0000396B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- mol
- acid chloride
- polycarbonates
- diphenols
- aromatic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920000515 polycarbonate Polymers 0.000 title claims description 31
- 239000004417 polycarbonate Substances 0.000 title claims description 31
- 238000000034 method Methods 0.000 title claims description 12
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title description 5
- 239000003063 flame retardant Substances 0.000 title description 4
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 4
- 150000001805 chlorine compounds Chemical class 0.000 claims description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 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 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- -1 halogen phenols Chemical class 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 5
- NYIBPWGZGSXURD-UHFFFAOYSA-N 3,4-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1Cl NYIBPWGZGSXURD-UHFFFAOYSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 3
- 229910052736 halogen Inorganic materials 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
- 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 2
- VMDRLEAPTZHOPG-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid hydrochloride Chemical compound Cl.OS(=O)(=O)C1=CC=C(Cl)C=C1 VMDRLEAPTZHOPG-UHFFFAOYSA-N 0.000 description 2
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- QDYGIMAMLUKRLQ-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;hydrochloride Chemical compound Cl.CC1=CC=C(S(O)(=O)=O)C=C1 QDYGIMAMLUKRLQ-UHFFFAOYSA-N 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- 239000003513 alkali Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000005501 phase interface Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- MPJLLBLFMGXUNW-UHFFFAOYSA-N 1,3,5-tribromocyclohexa-2,4-dien-1-ol Chemical compound OC1(Br)CC(Br)=CC(Br)=C1 MPJLLBLFMGXUNW-UHFFFAOYSA-N 0.000 description 1
- FREOGXBZEAMJQN-UHFFFAOYSA-N 2,4-dimethylbenzenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C(C)=C1 FREOGXBZEAMJQN-UHFFFAOYSA-N 0.000 description 1
- HXEQBGRXVLDXEI-UHFFFAOYSA-N 2,5-dichlorobenzenesulfonic acid hydrochloride Chemical compound Cl.OS(=O)(=O)C1=CC(Cl)=CC=C1Cl HXEQBGRXVLDXEI-UHFFFAOYSA-N 0.000 description 1
- BXCOSWRSIISQSL-UHFFFAOYSA-N 2,5-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(Cl)C(S(Cl)(=O)=O)=C1 BXCOSWRSIISQSL-UHFFFAOYSA-N 0.000 description 1
- BLDLRWQLBOJPEB-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfanylphenol Chemical class OC1=CC=CC=C1SC1=CC=CC=C1O BLDLRWQLBOJPEB-UHFFFAOYSA-N 0.000 description 1
- KYGLCUAXJICESS-UHFFFAOYSA-N 2-[2,3-di(propan-2-yl)phenyl]phenol Chemical class CC(C)C1=CC=CC(C=2C(=CC=CC=2)O)=C1C(C)C KYGLCUAXJICESS-UHFFFAOYSA-N 0.000 description 1
- PDBPQRIDVAJPQH-UHFFFAOYSA-N 2-chlorobenzenesulfonic acid hydrochloride Chemical compound Cl.OS(=O)(=O)C1=CC=CC=C1Cl PDBPQRIDVAJPQH-UHFFFAOYSA-N 0.000 description 1
- KMVZDSQHLDGKGV-UHFFFAOYSA-N 2-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=CC=C1S(Cl)(=O)=O KMVZDSQHLDGKGV-UHFFFAOYSA-N 0.000 description 1
- LIZNEYWXYFVEBF-UHFFFAOYSA-N 2-ethylbenzenesulfonyl chloride Chemical compound CCC1=CC=CC=C1S(Cl)(=O)=O LIZNEYWXYFVEBF-UHFFFAOYSA-N 0.000 description 1
- MCTATONZMSIRFG-UHFFFAOYSA-N 2-methylbenzenesulfonic acid;hydrochloride Chemical compound Cl.CC1=CC=CC=C1S(O)(=O)=O MCTATONZMSIRFG-UHFFFAOYSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
- GNYVVCRRZRVBDD-UHFFFAOYSA-N 3-chloro-4-methylbenzenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1Cl GNYVVCRRZRVBDD-UHFFFAOYSA-N 0.000 description 1
- RXARMNKWMWXBJK-UHFFFAOYSA-N 3-chlorobenzenesulfonic acid hydrochloride Chemical compound Cl.OS(=O)(=O)C1=CC=CC(Cl)=C1 RXARMNKWMWXBJK-UHFFFAOYSA-N 0.000 description 1
- OINWZUJVEXUHCC-UHFFFAOYSA-N 3-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=CC(S(Cl)(=O)=O)=C1 OINWZUJVEXUHCC-UHFFFAOYSA-N 0.000 description 1
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 1
- LACFLXDRFOQEFZ-UHFFFAOYSA-N 4-ethylbenzenesulfonyl chloride Chemical compound CCC1=CC=C(S(Cl)(=O)=O)C=C1 LACFLXDRFOQEFZ-UHFFFAOYSA-N 0.000 description 1
- ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 1
- VHBFBNCERXCECQ-UHFFFAOYSA-N 5-chloro-2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=C(Cl)C=C1S(Cl)(=O)=O VHBFBNCERXCECQ-UHFFFAOYSA-N 0.000 description 1
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LUCLFCZOEBZHPM-UHFFFAOYSA-N Cl.CC1=CC=C(S(O)(=O)=O)C(C)=C1 Chemical compound Cl.CC1=CC=C(S(O)(=O)=O)C(C)=C1 LUCLFCZOEBZHPM-UHFFFAOYSA-N 0.000 description 1
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- BQPJFNZAKMDFBG-UHFFFAOYSA-N anthracene-1-sulfonyl chloride Chemical class C1=CC=C2C=C3C(S(=O)(=O)Cl)=CC=CC3=CC2=C1 BQPJFNZAKMDFBG-UHFFFAOYSA-N 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- OPZGHHMHHWXKAA-UHFFFAOYSA-N benzenesulfonic acid;hydrochloride Chemical compound Cl.OS(=O)(=O)C1=CC=CC=C1 OPZGHHMHHWXKAA-UHFFFAOYSA-N 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- DASJFYAPNPUBGG-UHFFFAOYSA-N naphthalene-1-sulfonyl chloride Chemical class C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 DASJFYAPNPUBGG-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- YYSWKSJKAKNXHB-UHFFFAOYSA-N phenanthrene-1-sulfonyl chloride Chemical class C1=CC2=CC=CC=C2C2=C1C(S(=O)(=O)Cl)=CC=C2 YYSWKSJKAKNXHB-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 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
- C08G64/14—Aromatic polycarbonates not containing aliphatic unsaturation containing a chain-terminating or -crosslinking agent
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S260/00—Chemistry of carbon compounds
- Y10S260/24—Flameproof
Definitions
- the present invention relates to the production of aromatic polycarbonates with an average molecular weight between 10,000 and 100,000 by the known two-phase interface process from diphenols, preferably from halogen-free diphenols, using chain terminators, characterized in that aromatic monosulfonic acid chlorides in amounts of 2 mol -% to 20 mol%, preferably in amounts of 2.5 mol% to 10 mol%, based on moles of the diphenols used.
- the present invention also relates to the aromatic polycarbonates obtained by the process according to the invention.
- the polycarbonates obtained according to the invention have improved flame resistance.
- the improvement of the flame-retardant properties of the aromatic thermoplastic polycarbonates has already been attempted and achieved in various ways, although disadvantages with other polycarbonate properties have to be accepted occasionally.
- halogen phenols can also be used as flame-retardant chain terminators.
- aromatic monosulfonic acid chlorides can be used for the process according to the invention, for example unsubstituted and substituted benzenesulfonic acid chlorides, unsubstituted and substituted naphthalenesulfonic acid chlorides, unsubstituted and substituted anthracene sulfonic acid chlorides and unsubstituted and substituted phenanthrene sulfonic acid chlorides.
- substituents are understood to mean, for example, alkyl, cycloalkyl, aryl or halogen.
- Suitable benzenesulfonic acid chlorides according to the invention are those of the formula I. wherein R, to R 5 are the same or different and are H, alkyl, preferably C, to C 4 , cycloalkyl, preferably C 5 to C 6 , aryl, preferably C 6 to C 16 , or halogen, preferably chlorine or bromine.
- the production of polycarbonates by the phase interface process is known.
- the polycarbonates are obtained by reacting diphenols, in particular dihydroxydiarylalkanes or -cycloalkanes with phosgene, in addition to the unsubstituted dihydroxydiarylalkanes or -cycloalkanes, those whose aryl radicals are substituted in the o-position to the phenolic hydroxyl groups are also suitable.
- the polycarbonates produced by the phase interface process can also be branched in a known manner.
- the known catalysts such as triethylamine and the usual solvents, reaction temperatures and amounts of alkali from the two-phase interface process are also common.
- Suitable diphenols are, for example, hydroquinone, resorcinol, 4,4'-dihydroxydiphenyl, bis (hydroxyphenyl) alkanes, such as, for example, C 1 -C 8 -alkylene or.
- a-bis (hydroxyphenyl) diisopropylbenzenes and the corresponding ring-alkylated or ring-halogenated compounds are suitable, for example phenol A), bis (4-hydroxy-3,5-dibromophenyl) propane-2,2 (tetrabromobisphenol A), bis (4-hydroxy-3,5-dimethyl-phenyl) propane-2,2 tetramethylbisphenol A), bis - (4 - hydroxy - 3 - methyl - phenyl) - propane - 2,2, bis - (4 - hydroxy - phenyl) cyclohexane-1,1 (bisphenol Z) as well as based on trinuclear bisphenols like a, a - bis - (4
- the polycarbonates from halogen-free diphenols are preferred.
- the flame-retardant polycarbonates produced according to the invention are distinguished by an improved flame resistance compared to the conventional polycarbonates terminated with monofunctional phenols. In this way, the polycarbonates according to the invention achieve better fire ratings or considerably shorter afterburning times, depending on the molecular weight or chain regulator content.
- Approx. 454 parts of 4,4'-dihydroxydiphenyl-2,2-propane and 9.5 parts of p-tert-butylphenol are suspended in 1.5 l of water.
- the oxygen is removed from the reaction mixture by stirring for 15 min.
- nitrogen is passed through the reaction mixture.
- 355 parts of 45% sodium hydroxide solution and 1000 parts of methylene chloride are added.
- the mixture is cooled to 25 ° C. While maintaining this temperature by cooling, 237 parts of phosgene are removed over a period of 120 min. admitted.
- An additional amount of 75 parts of a 45% sodium hydroxide solution is added after 15-30 minutes or after the phosgene uptake has begun.
- a solution is prepared from 3.192 kg of 2,2-bis (4-hydroxyphenyl) propane (bisphenol A) (14 mol), 2.53 kg of 45% strength aqueous sodium hydroxide solution and 15 l of distilled water. After adding 34 kg of methylene chloride, 80.8 g. Benzenesulfonic acid chloride (3.27 mol%), dissolved in 1 kg of methylene chloride, added at room temperature. At 20-25 ° C, 2.64 kg of phosgene are introduced. By adding a further 26.3 kg of 6.5% sodium hydroxide solution during the phosgenation, the pH is kept at 13-14. Then 15 ml of triethylamine are added and stirring is continued for 30 minutes.
- the fire behavior was measured according to UL Bull 94, test rod thickness 1/16 "on tempered test rods (130'C, 2 days).
- the afterburn times after the 2nd flame exposure are determined with the stopwatch; Average of 5 different measurements.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2732556 | 1977-07-19 | ||
| DE19772732556 DE2732556A1 (de) | 1977-07-19 | 1977-07-19 | Verfahren zur herstellung von flammhemmenden polycarbonaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0000396A1 EP0000396A1 (de) | 1979-01-24 |
| EP0000396B1 true EP0000396B1 (de) | 1980-07-23 |
Family
ID=6014277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP78100379A Expired EP0000396B1 (de) | 1977-07-19 | 1978-07-12 | Verfahren zur Herstellung von flammhemmenden Polycarbonaten |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4188475A (enrdf_load_stackoverflow) |
| EP (1) | EP0000396B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS5421497A (enrdf_load_stackoverflow) |
| DE (2) | DE2732556A1 (enrdf_load_stackoverflow) |
| IT (1) | IT1106182B (enrdf_load_stackoverflow) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5625110A (en) * | 1978-12-18 | 1981-03-10 | Bristol Myers Co | Antibacterial |
| US4403087A (en) * | 1981-09-28 | 1983-09-06 | General Electric Company | Polycarbonates chain terminated with sulfonic acid salt containing phenols |
| US4469860A (en) * | 1981-09-28 | 1984-09-04 | General Electric Company | Aromatic polycarbonate resin end capped with hydroxy arylene sulfonate |
| DE3150273A1 (de) * | 1981-12-18 | 1983-06-30 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von polycarbonaten mit sulfonanilid-endgruppen |
| DE3225884A1 (de) * | 1982-07-10 | 1984-01-12 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von polycarbonaten mit n-alkylperfluoralkylsulfonamid-endgruppen |
| JPS60501212A (ja) * | 1983-05-04 | 1985-08-01 | ゼネラル エレクトリツク カンパニイ | 難燃性末端キヤツプポリカ−ボネ−トを含む組成物 |
| IT1214645B (it) * | 1985-12-19 | 1990-01-18 | Enichem Polimeri | Policarbonati ramificati contenenti composti aromatici binucleari. |
| JP2001520435A (ja) | 1997-10-15 | 2001-10-30 | ザ ダウ ケミカル カンパニー | 電子伝導性ポリマー類 |
| US20080014446A1 (en) * | 2004-10-07 | 2008-01-17 | General Electric Company | Window shade and a multi-layered article, and methods of making the same |
| US7557153B2 (en) * | 2005-10-31 | 2009-07-07 | Sabic Innovative Plastics Ip Bv | Ionizing radiation stable thermoplastic composition, method of making, and articles formed therefrom |
| US7528212B2 (en) * | 2005-11-18 | 2009-05-05 | Sabic Innovative Plastics Ip B.V. | Ionizing radiation stable thermoplastic composition, method of making, and articles formed therefrom |
| US20080081892A1 (en) * | 2006-09-29 | 2008-04-03 | General Electric Company | Thermoplastic compositions, methods of making, and articles formed therefrom |
| US9803510B2 (en) | 2011-04-18 | 2017-10-31 | Holtec International | Autonomous self-powered system for removing thermal energy from pools of liquid heated by radioactive materials, and method of the same |
| US8445568B2 (en) * | 2008-09-25 | 2013-05-21 | Sabic Innovative Plastics Ip B.V. | Flame retardant thermoplastic composition and articles formed therefrom |
| US8771829B2 (en) * | 2008-09-25 | 2014-07-08 | Sabic Innovative Plastics Ip B.V. | Flame retardant thermoplastic polymer composition, method of manufacture, and articles formed therefrom |
| US20100280159A1 (en) * | 2008-09-25 | 2010-11-04 | Christianus Johannes Jacobus Maas | Flame retardant thermoplastic composition and articles formed therefrom |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB964711A (en) | 1960-03-31 | 1964-07-22 | Teikoku Jinzo Kenshi Kk | Modified polyesters and the method of preparation thereof |
| US3177179A (en) * | 1960-05-31 | 1965-04-06 | Dow Chemical Co | Chain terminated polycarbonates |
| US3240756A (en) * | 1961-03-02 | 1966-03-15 | Allied Chem | Continuous addition of phenolic chain terminator in bisphenol polycarbonate production by emulsion polymerization |
| US3398120A (en) * | 1963-07-16 | 1968-08-20 | Hooker Chemical Corp | Polyesters of diacid halide, alkyl bisphenol and glycol |
| US3933734A (en) * | 1973-12-28 | 1976-01-20 | General Electric Company | Flame retardant polycarbonate composition |
| US4020045A (en) * | 1976-02-26 | 1977-04-26 | The Dow Chemical Company | Process for controlling the molecular weight of aromatic polycarbonates |
-
1977
- 1977-07-19 DE DE19772732556 patent/DE2732556A1/de not_active Withdrawn
-
1978
- 1978-06-30 US US05/920,932 patent/US4188475A/en not_active Expired - Lifetime
- 1978-07-12 EP EP78100379A patent/EP0000396B1/de not_active Expired
- 1978-07-12 DE DE7878100379T patent/DE2860055D1/de not_active Expired
- 1978-07-17 JP JP8619778A patent/JPS5421497A/ja active Granted
- 1978-07-17 IT IT50325/78A patent/IT1106182B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6228809B2 (enrdf_load_stackoverflow) | 1987-06-23 |
| US4188475A (en) | 1980-02-12 |
| IT1106182B (it) | 1985-11-11 |
| DE2732556A1 (de) | 1979-02-01 |
| EP0000396A1 (de) | 1979-01-24 |
| DE2860055D1 (en) | 1980-11-13 |
| IT7850325A0 (it) | 1978-07-17 |
| JPS5421497A (en) | 1979-02-17 |
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