DE2113347C2 - Tetraphenol, Verfahren zu seiner Herstellung und Verwendung zur Herstellung von verzweigten Polycarbonaten - Google Patents
Tetraphenol, Verfahren zu seiner Herstellung und Verwendung zur Herstellung von verzweigten PolycarbonatenInfo
- Publication number
- DE2113347C2 DE2113347C2 DE19712113347 DE2113347A DE2113347C2 DE 2113347 C2 DE2113347 C2 DE 2113347C2 DE 19712113347 DE19712113347 DE 19712113347 DE 2113347 A DE2113347 A DE 2113347A DE 2113347 C2 DE2113347 C2 DE 2113347C2
- Authority
- DE
- Germany
- Prior art keywords
- bis
- benzene
- production
- tetraphenol
- dihydroxy
- 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
- 239000004417 polycarbonate Substances 0.000 title claims description 14
- 229920000515 polycarbonate Polymers 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 38
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000243 solution Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000001125 extrusion Methods 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000000149 argon plasma sintering Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- LTGXPINWZFIICV-UHFFFAOYSA-N 1,4-dibenzylbenzene Chemical compound C=1C=C(CC=2C=CC=CC=2)C=CC=1CC1=CC=CC=C1 LTGXPINWZFIICV-UHFFFAOYSA-N 0.000 description 2
- STOZLVQMAVNMBX-UHFFFAOYSA-N 2-[[6-hydroxy-5-[(2-hydroxy-5-methylphenyl)methylidene]-3-methylcyclohex-3-en-1-ylidene]methyl]-4-methylphenol Chemical compound OC1C(=CC=2C(=CC=C(C)C=2)O)CC(C)=CC1=CC1=CC(C)=CC=C1O STOZLVQMAVNMBX-UHFFFAOYSA-N 0.000 description 2
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 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 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- NPENBPVOAXERED-UHFFFAOYSA-N (4-benzoylphenyl)-phenylmethanone Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 NPENBPVOAXERED-UHFFFAOYSA-N 0.000 description 1
- BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 208000000260 Warts Diseases 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/18—Preparation of halogenated hydrocarbons by replacement by halogens of oxygen atoms of carbonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/18—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving halogen atoms of halogenated compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712113347 DE2113347C2 (de) | 1971-03-19 | 1971-03-19 | Tetraphenol, Verfahren zu seiner Herstellung und Verwendung zur Herstellung von verzweigten Polycarbonaten |
| CA121,651A CA986128A (en) | 1971-03-19 | 1971-08-30 | Tetraphenol |
| NL7112093A NL176554C (nl) | 1971-03-19 | 1971-09-02 | Werkwijze voor de bereiding van tetrafenol, alsmede werkwijze voor de bereiding van macromoleculaire kunststoffen. |
| GB4098271A GB1333812A (en) | 1971-03-19 | 1971-09-02 | Tetraphenol its preparation and its use |
| BE772095A BE772095A (fr) | 1971-03-19 | 1971-09-02 | Nouveau tetraphenol et son procede de preparation |
| JP6800171A JPS5414101B1 (cg-RX-API-DMAC7.html) | 1971-03-19 | 1971-09-03 | |
| BR582571A BR7105825D0 (pt) | 1971-03-19 | 1971-09-03 | Processo de preparacao de 1,4-bis-(4',4"-de-hidroxitrifenil metil)-benzeno |
| FR7131942A FR2130055B1 (cg-RX-API-DMAC7.html) | 1971-03-19 | 1971-09-03 | |
| ES394799A ES394799A1 (es) | 1971-03-19 | 1971-09-04 | Procedimiento para la obtencion de 1,4 - bis -( 4, 4 dihi- droxi - trifenil-metil) benceno. |
| CA211,761A CA1016294A (en) | 1971-03-19 | 1974-10-18 | Branched polycarbonates |
| US05/558,049 US4001183A (en) | 1971-03-19 | 1975-03-13 | Tetraphenol containing polycarbonates |
| JP309279A JPS54139699A (en) | 1971-03-19 | 1979-01-17 | Method of using tetraphenol in synthesis of branched polycarbonate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712113347 DE2113347C2 (de) | 1971-03-19 | 1971-03-19 | Tetraphenol, Verfahren zu seiner Herstellung und Verwendung zur Herstellung von verzweigten Polycarbonaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2113347A1 DE2113347A1 (de) | 1972-10-26 |
| DE2113347C2 true DE2113347C2 (de) | 1984-04-26 |
Family
ID=5802100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712113347 Expired DE2113347C2 (de) | 1971-03-19 | 1971-03-19 | Tetraphenol, Verfahren zu seiner Herstellung und Verwendung zur Herstellung von verzweigten Polycarbonaten |
Country Status (9)
| Country | Link |
|---|---|
| JP (2) | JPS5414101B1 (cg-RX-API-DMAC7.html) |
| BE (1) | BE772095A (cg-RX-API-DMAC7.html) |
| BR (1) | BR7105825D0 (cg-RX-API-DMAC7.html) |
| CA (1) | CA986128A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2113347C2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES394799A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2130055B1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1333812A (cg-RX-API-DMAC7.html) |
| NL (1) | NL176554C (cg-RX-API-DMAC7.html) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3378125D1 (en) | 1982-09-10 | 1988-11-03 | Bayer Ag | Flame-retardant polymer mixtures |
| CA1289290C (en) | 1985-04-11 | 1991-09-17 | John V. Bailey | Stabilized polycarbonates |
| DE4013112A1 (de) * | 1990-04-25 | 1991-11-07 | Bayer Ag | Stabilisierte thermoplastische formmassen |
| DE4013113A1 (de) * | 1990-04-25 | 1991-10-31 | Bayer Ag | Stabilisierte thermoplastische formmassen |
| DE102009029050A1 (de) * | 2009-08-31 | 2011-03-03 | Evonik Oxeno Gmbh | Organophosphorverbindungen basierend auf Tetraphenol(TP)-substituierten Strukturen |
| JP5421174B2 (ja) * | 2010-04-01 | 2014-02-19 | 帝人株式会社 | 分岐状ポリカーボネート樹脂の製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1768901A1 (de) * | 1968-07-11 | 1971-12-23 | Dynamit Nobel Ag | Verfahren zur Herstellung von 4,4'-Dioxytetraphenylmethan |
-
1971
- 1971-03-19 DE DE19712113347 patent/DE2113347C2/de not_active Expired
- 1971-08-30 CA CA121,651A patent/CA986128A/en not_active Expired
- 1971-09-02 GB GB4098271A patent/GB1333812A/en not_active Expired
- 1971-09-02 BE BE772095A patent/BE772095A/xx unknown
- 1971-09-02 NL NL7112093A patent/NL176554C/xx not_active IP Right Cessation
- 1971-09-03 BR BR582571A patent/BR7105825D0/pt unknown
- 1971-09-03 JP JP6800171A patent/JPS5414101B1/ja active Pending
- 1971-09-03 FR FR7131942A patent/FR2130055B1/fr not_active Expired
- 1971-09-04 ES ES394799A patent/ES394799A1/es not_active Expired
-
1979
- 1979-01-17 JP JP309279A patent/JPS54139699A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54139699A (en) | 1979-10-30 |
| BR7105825D0 (pt) | 1973-03-13 |
| CA986128A (en) | 1976-03-23 |
| JPS5547047B2 (cg-RX-API-DMAC7.html) | 1980-11-27 |
| NL7112093A (cg-RX-API-DMAC7.html) | 1972-09-21 |
| JPS5414101B1 (cg-RX-API-DMAC7.html) | 1979-06-05 |
| FR2130055B1 (cg-RX-API-DMAC7.html) | 1973-05-25 |
| FR2130055A1 (cg-RX-API-DMAC7.html) | 1972-11-03 |
| GB1333812A (en) | 1973-10-17 |
| BE772095A (fr) | 1972-03-02 |
| DE2113347A1 (de) | 1972-10-26 |
| NL176554C (nl) | 1985-05-01 |
| NL176554B (nl) | 1984-12-03 |
| ES394799A1 (es) | 1974-09-01 |
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Ipc: C07C 39/15 |
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| 8181 | Inventor (new situation) |
Free format text: FREITAG, DIETER, DR. HABERLAND, ULRICH, DR. KRIMM, HEINRICH, DR., 4150 KREFELD, DE |
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| D2 | Grant after examination | ||
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