CH633505A5 - Process for the preparation of sterically hindered bisphenols or polyphenols - Google Patents
Process for the preparation of sterically hindered bisphenols or polyphenols Download PDFInfo
- Publication number
- CH633505A5 CH633505A5 CH731077A CH731077A CH633505A5 CH 633505 A5 CH633505 A5 CH 633505A5 CH 731077 A CH731077 A CH 731077A CH 731077 A CH731077 A CH 731077A CH 633505 A5 CH633505 A5 CH 633505A5
- Authority
- CH
- Switzerland
- Prior art keywords
- tert
- butyl
- bis
- mol
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 49
- 235000013824 polyphenols Nutrition 0.000 title claims description 13
- 150000008442 polyphenolic compounds Chemical class 0.000 title claims description 12
- 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 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 8
- 229930185605 Bisphenol Natural products 0.000 title description 3
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 claims description 15
- 150000001299 aldehydes Chemical class 0.000 claims description 13
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000001241 acetals Chemical class 0.000 claims description 9
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 7
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 6
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 5
- 239000003377 acid catalyst Substances 0.000 claims description 5
- -1 cyclic aldehyde Chemical class 0.000 claims description 5
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 claims description 4
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 claims description 4
- 229920002866 paraformaldehyde Polymers 0.000 claims description 4
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 32
- 239000000047 product Substances 0.000 description 27
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 17
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 16
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 16
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 11
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 9
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000002351 wastewater Substances 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 3
- VDOJQPKPGQMNDA-UHFFFAOYSA-N 2,6-ditert-butyl-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VDOJQPKPGQMNDA-UHFFFAOYSA-N 0.000 description 3
- PGOFYKDJABUOQA-UHFFFAOYSA-N 2-benzyl-4-methyl-6-(2-methylpentan-2-yl)phenol Chemical compound CCCC(C)(C)C1=CC(C)=CC(CC=2C=CC=CC=2)=C1O PGOFYKDJABUOQA-UHFFFAOYSA-N 0.000 description 3
- ZYJZBYZJLPVZHR-UHFFFAOYSA-N 2-tert-butyl-4-methyl-6-(2-phenylpropan-2-yl)phenol Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C=2C=CC=CC=2)=C1 ZYJZBYZJLPVZHR-UHFFFAOYSA-N 0.000 description 3
- JXGACSBVPLKCJV-UHFFFAOYSA-N 2-tert-butyl-6-cyclohexyl-4-methylphenol Chemical compound CC(C)(C)C1=CC(C)=CC(C2CCCCC2)=C1O JXGACSBVPLKCJV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- ZXLSNLZXWMSDNF-UHFFFAOYSA-N 2,4-dimethyl-6-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)CC(C)(C)C)=C1 ZXLSNLZXWMSDNF-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000020335 dealkylation Effects 0.000 description 2
- 238000006900 dealkylation reaction Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 231100000086 high toxicity Toxicity 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- LXWZXEJDKYWBOW-UHFFFAOYSA-N 2,4-ditert-butyl-6-[(3,5-ditert-butyl-2-hydroxyphenyl)methyl]phenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)C)C(C)(C)C)O)=C1O LXWZXEJDKYWBOW-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- FCIMDZFOYJBMLV-UHFFFAOYSA-N 2-[(2-hydroxy-3,5-dimethylphenyl)methyl]-4,6-dimethylphenol Chemical compound CC1=CC(C)=C(O)C(CC=2C(=C(C)C=C(C)C=2)O)=C1 FCIMDZFOYJBMLV-UHFFFAOYSA-N 0.000 description 1
- AKNMPWVTPUHKCG-UHFFFAOYSA-N 2-cyclohexyl-6-[(3-cyclohexyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound OC=1C(C2CCCCC2)=CC(C)=CC=1CC(C=1O)=CC(C)=CC=1C1CCCCC1 AKNMPWVTPUHKCG-UHFFFAOYSA-N 0.000 description 1
- LZHCVNIARUXHAL-UHFFFAOYSA-N 2-tert-butyl-4-ethylphenol Chemical compound CCC1=CC=C(O)C(C(C)(C)C)=C1 LZHCVNIARUXHAL-UHFFFAOYSA-N 0.000 description 1
- MDWVSAYEQPLWMX-UHFFFAOYSA-N 4,4'-Methylenebis(2,6-di-tert-butylphenol) Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MDWVSAYEQPLWMX-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- TWWSMHPNERSWRN-UHFFFAOYSA-N acetaldehyde diisopropyl acetal Natural products CC(C)OC(C)OC(C)C TWWSMHPNERSWRN-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229920005565 cyclic polymer Polymers 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229920003049 isoprene rubber Polymers 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 1
- 229960003868 paraldehyde Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C37/20—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 using aldehydes or ketones
-
- 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
- C07C37/115—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 using acetals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU762372253A SU732232A1 (ru) | 1976-06-14 | 1976-06-14 | Способ получени пространственно- затрудненных бис- или полифенолов |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH633505A5 true CH633505A5 (en) | 1982-12-15 |
Family
ID=20665542
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH731077A CH633505A5 (en) | 1976-06-14 | 1977-06-14 | Process for the preparation of sterically hindered bisphenols or polyphenols |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5315349A (cg-RX-API-DMAC10.html) |
| AT (1) | AT352706B (cg-RX-API-DMAC10.html) |
| BE (1) | BE855676A (cg-RX-API-DMAC10.html) |
| BR (1) | BR7703857A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1109894A (cg-RX-API-DMAC10.html) |
| CH (1) | CH633505A5 (cg-RX-API-DMAC10.html) |
| DE (1) | DE2726762C3 (cg-RX-API-DMAC10.html) |
| DK (1) | DK146908C (cg-RX-API-DMAC10.html) |
| FI (1) | FI65421C (cg-RX-API-DMAC10.html) |
| FR (1) | FR2354988A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1555728A (cg-RX-API-DMAC10.html) |
| IE (1) | IE45388B1 (cg-RX-API-DMAC10.html) |
| IT (1) | IT1114877B (cg-RX-API-DMAC10.html) |
| NL (1) | NL172053C (cg-RX-API-DMAC10.html) |
| NO (1) | NO147024C (cg-RX-API-DMAC10.html) |
| PT (1) | PT66676B (cg-RX-API-DMAC10.html) |
| SE (1) | SE442632B (cg-RX-API-DMAC10.html) |
| SU (1) | SU732232A1 (cg-RX-API-DMAC10.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0110830A1 (de) * | 1982-11-25 | 1984-06-13 | Ciba-Geigy Ag | Neue benzylierte Phenole |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4222884A (en) * | 1978-12-04 | 1980-09-16 | Ethyl Corporation | Antioxidant |
| US6207866B1 (en) * | 1997-07-11 | 2001-03-27 | Nippon Petrochemicals Company, Limited | Method for producing diarylmethane or its derivatives |
| JP2000016952A (ja) | 1998-07-01 | 2000-01-18 | Nippon Petrochem Co Ltd | 炭化水素の製造方法 |
| RU2150461C1 (ru) * | 1999-03-01 | 2000-06-10 | ЗАО Стерлитамакский нефтехимический завод | Способ получения 2,2'-метиленбис-(4-метил-6-трет-бутилфенола) |
| JP4376367B2 (ja) | 1999-09-20 | 2009-12-02 | 新日本石油株式会社 | 炭化水素溶剤およびそれを用いた感圧複写材料 |
| CN105859771B (zh) * | 2016-03-25 | 2018-09-14 | 维思普新材料（苏州）有限公司 | 一种芳基膦酸盐成核剂的制备方法 |
-
1976
- 1976-06-14 SU SU762372253A patent/SU732232A1/ru active
-
1977
- 1977-06-13 CA CA280,418A patent/CA1109894A/en not_active Expired
- 1977-06-13 NL NLAANVRAGE7706496,A patent/NL172053C/xx not_active IP Right Cessation
- 1977-06-13 SE SE7706829A patent/SE442632B/xx not_active IP Right Cessation
- 1977-06-13 DK DK260377A patent/DK146908C/da not_active IP Right Cessation
- 1977-06-13 AT AT414877A patent/AT352706B/de not_active IP Right Cessation
- 1977-06-13 NO NO772056A patent/NO147024C/no unknown
- 1977-06-13 IT IT24626/77A patent/IT1114877B/it active
- 1977-06-14 GB GB24793/77A patent/GB1555728A/en not_active Expired
- 1977-06-14 BR BR7703857A patent/BR7703857A/pt unknown
- 1977-06-14 IE IE1216/77A patent/IE45388B1/en unknown
- 1977-06-14 BE BE178436A patent/BE855676A/xx not_active IP Right Cessation
- 1977-06-14 JP JP6949577A patent/JPS5315349A/ja active Granted
- 1977-06-14 FR FR7718180A patent/FR2354988A1/fr active Granted
- 1977-06-14 FI FI771872A patent/FI65421C/fi not_active IP Right Cessation
- 1977-06-14 DE DE2726762A patent/DE2726762C3/de not_active Expired
- 1977-06-14 CH CH731077A patent/CH633505A5/de not_active IP Right Cessation
- 1977-06-15 PT PT66676A patent/PT66676B/pt unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0110830A1 (de) * | 1982-11-25 | 1984-06-13 | Ciba-Geigy Ag | Neue benzylierte Phenole |
Also Published As
| Publication number | Publication date |
|---|---|
| BR7703857A (pt) | 1978-04-25 |
| NO147024C (no) | 1983-01-26 |
| DE2726762C3 (de) | 1981-10-15 |
| FI65421C (fi) | 1984-05-10 |
| IT1114877B (it) | 1986-01-27 |
| IE45388B1 (en) | 1982-08-11 |
| FI65421B (fi) | 1984-01-31 |
| DK146908C (da) | 1984-07-23 |
| GB1555728A (en) | 1979-11-14 |
| NO147024B (no) | 1982-10-11 |
| ATA414877A (de) | 1979-03-15 |
| DE2726762A1 (de) | 1977-12-22 |
| SE7706829L (sv) | 1977-12-15 |
| FI771872A7 (cg-RX-API-DMAC10.html) | 1977-12-15 |
| CA1109894A (en) | 1981-09-29 |
| NO772056L (no) | 1977-12-15 |
| SE442632B (sv) | 1986-01-20 |
| DK260377A (da) | 1977-12-15 |
| BE855676A (fr) | 1977-12-14 |
| PT66676A (en) | 1977-07-01 |
| IE45388L (en) | 1977-12-14 |
| NL172053B (nl) | 1983-02-01 |
| DK146908B (da) | 1984-02-06 |
| FR2354988A1 (fr) | 1978-01-13 |
| FR2354988B1 (cg-RX-API-DMAC10.html) | 1981-11-27 |
| JPS5315349A (en) | 1978-02-13 |
| PT66676B (en) | 1978-11-15 |
| AT352706B (de) | 1979-10-10 |
| DE2726762B2 (de) | 1980-08-21 |
| JPS558500B2 (cg-RX-API-DMAC10.html) | 1980-03-04 |
| SU732232A1 (ru) | 1980-05-05 |
| NL7706496A (nl) | 1977-12-16 |
| NL172053C (nl) | 1983-07-01 |
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