SU732232A1 - Способ получени пространственно- затрудненных бис- или полифенолов - Google Patents
Способ получени пространственно- затрудненных бис- или полифенолов Download PDFInfo
- Publication number
- SU732232A1 SU732232A1 SU762372253A SU2372253A SU732232A1 SU 732232 A1 SU732232 A1 SU 732232A1 SU 762372253 A SU762372253 A SU 762372253A SU 2372253 A SU2372253 A SU 2372253A SU 732232 A1 SU732232 A1 SU 732232A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- tert
- butyl
- mol
- polyphenols
- reaction
- Prior art date
Links
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 150000008442 polyphenolic compounds Chemical class 0.000 title claims abstract description 8
- 235000013824 polyphenols Nutrition 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims description 19
- 239000002253 acid Substances 0.000 claims abstract description 9
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 3
- 229920000642 polymer Polymers 0.000 claims abstract description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 4
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims abstract 2
- 239000003054 catalyst Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- -1 or cycloaclyl Chemical group 0.000 claims description 8
- 239000002351 wastewater Substances 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000003729 cation exchange resin Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 229940023913 cation exchange resins Drugs 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 229930185605 Bisphenol Natural products 0.000 abstract description 4
- 239000003381 stabilizer Substances 0.000 abstract description 4
- 231100000252 nontoxic Toxicity 0.000 abstract description 2
- 230000003000 nontoxic effect Effects 0.000 abstract description 2
- 239000004033 plastic Substances 0.000 abstract description 2
- 229920003023 plastic Polymers 0.000 abstract description 2
- 238000010186 staining Methods 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 229920003052 natural elastomer Polymers 0.000 abstract 1
- 229920001194 natural rubber Polymers 0.000 abstract 1
- 229920003051 synthetic elastomer Polymers 0.000 abstract 1
- 239000005061 synthetic rubber Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 38
- 239000000047 product Substances 0.000 description 27
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 10
- 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 8
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 8
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 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
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 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 2
- 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 2
- 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 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- ZVAVMLFUZSRPPQ-UHFFFAOYSA-N 2,3-ditert-butyl-4-ethylphenol Chemical compound CCC1=CC=C(O)C(C(C)(C)C)=C1C(C)(C)C ZVAVMLFUZSRPPQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CJWNFAKWHDOUKL-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)phenol Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1 CJWNFAKWHDOUKL-UHFFFAOYSA-N 0.000 description 1
- AHKRMDMQOAEIKN-UHFFFAOYSA-N 2-benzyl-3-methylphenol Chemical compound CC1=CC=CC(O)=C1CC1=CC=CC=C1 AHKRMDMQOAEIKN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 239000007848 Bronsted acid Substances 0.000 description 1
- DLOLXMWDHQVMHG-UHFFFAOYSA-N CC=1C=C(C(=C(C=1)CCC)O)CC1=CC=CC=C1 Chemical compound CC=1C=C(C(=C(C=1)CCC)O)CC1=CC=CC=C1 DLOLXMWDHQVMHG-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- UAJUXJSXCLUTNU-UHFFFAOYSA-N pranlukast Chemical compound C=1C=C(OCCCCC=2C=CC=CC=2)C=CC=1C(=O)NC(C=1)=CC=C(C(C=2)=O)C=1OC=2C=1N=NNN=1 UAJUXJSXCLUTNU-UHFFFAOYSA-N 0.000 description 1
- 229960004583 pranlukast Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 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)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU762372253A SU732232A1 (ru) | 1976-06-14 | 1976-06-14 | Способ получени пространственно- затрудненных бис- или полифенолов |
| IT24626/77A IT1114877B (it) | 1976-06-14 | 1977-06-13 | Procedimento per ottenere bis-o polifenoli ad impedimento sterico |
| NLAANVRAGE7706496,A NL172053C (nl) | 1976-06-14 | 1977-06-13 | Werkwijze voor de bereiding van sterisch gehinderde bis- of polyfenolen. |
| AT414877A AT352706B (de) | 1976-06-14 | 1977-06-13 | Verfahren zur herstellung von sterisch- gehinderten bis- oder polyphenolen |
| NO772056A NO147024C (no) | 1976-06-14 | 1977-06-13 | Fremgangsmaate til fremstilling av sterisk hindrede bis- eller polyfenoler. |
| CA280,418A CA1109894A (en) | 1976-06-14 | 1977-06-13 | Method for preparing sterically hindered bis- or polyphenols |
| SE7706829A SE442632B (sv) | 1976-06-14 | 1977-06-13 | Forfarande for framstellning av steriskt hindrade bis- eller polyfenoler |
| DK260377A DK146908C (da) | 1976-06-14 | 1977-06-13 | Fremgangsmaade til fremstilling af sterisk hindrede bis- eller polyphenoler |
| IE1216/77A IE45388B1 (en) | 1976-06-14 | 1977-06-14 | Preparation of sterically hindered polyphenols |
| JP6949577A JPS5315349A (en) | 1976-06-14 | 1977-06-14 | Process for preparing bissor polyphenol having steric hindbance |
| BE178436A BE855676A (fr) | 1976-06-14 | 1977-06-14 | Procede de preparation de bis-phenols ou de polyphenols a empechements steriques et produits obtenus |
| FI771872A FI65421C (fi) | 1976-06-14 | 1977-06-14 | Foerfarande foer framstaellning av steriskt hindrade bis- och polyfenoler |
| BR7703857A BR7703857A (pt) | 1976-06-14 | 1977-06-14 | Processo para a preparacao de fenois ou polifenois estericamente bloqueados |
| FR7718180A FR2354988A1 (fr) | 1976-06-14 | 1977-06-14 | Procede de preparation de bisphenols ou de polyphenols a empechements steriques |
| DE2726762A DE2726762C3 (de) | 1976-06-14 | 1977-06-14 | Verfahren zur Herstellung von sterisch gehinderten Bis- oder Polyphenolen |
| CH731077A CH633505A5 (en) | 1976-06-14 | 1977-06-14 | Process for the preparation of sterically hindered bisphenols or polyphenols |
| GB24793/77A GB1555728A (en) | 1976-06-14 | 1977-06-14 | Preparation of sterically hindered polyphenols |
| PT66676A PT66676B (en) | 1976-06-14 | 1977-06-15 | Method for preparing sterically-hindered bis- or polyphenols |
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 |
|---|---|
| SU732232A1 true SU732232A1 (ru) | 1980-05-05 |
Family
ID=20665542
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762372253A SU732232A1 (ru) | 1976-06-14 | 1976-06-14 | Способ получени пространственно- затрудненных бис- или полифенолов |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5315349A (enExample) |
| AT (1) | AT352706B (enExample) |
| BE (1) | BE855676A (enExample) |
| BR (1) | BR7703857A (enExample) |
| CA (1) | CA1109894A (enExample) |
| CH (1) | CH633505A5 (enExample) |
| DE (1) | DE2726762C3 (enExample) |
| DK (1) | DK146908C (enExample) |
| FI (1) | FI65421C (enExample) |
| FR (1) | FR2354988A1 (enExample) |
| GB (1) | GB1555728A (enExample) |
| IE (1) | IE45388B1 (enExample) |
| IT (1) | IT1114877B (enExample) |
| NL (1) | NL172053C (enExample) |
| NO (1) | NO147024C (enExample) |
| PT (1) | PT66676B (enExample) |
| SE (1) | SE442632B (enExample) |
| SU (1) | SU732232A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4222884A (en) * | 1978-12-04 | 1980-09-16 | Ethyl Corporation | Antioxidant |
| US4532059A (en) * | 1982-11-25 | 1985-07-30 | Ciba-Geigy Corporation | Benzylated phenols |
| 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
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 (enExample) | 1977-12-15 |
| CA1109894A (en) | 1981-09-29 |
| CH633505A5 (en) | 1982-12-15 |
| 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 (enExample) | 1981-11-27 |
| JPS5315349A (en) | 1978-02-13 |
| PT66676B (en) | 1978-11-15 |
| AT352706B (de) | 1979-10-10 |
| DE2726762B2 (de) | 1980-08-21 |
| JPS558500B2 (enExample) | 1980-03-04 |
| NL7706496A (nl) | 1977-12-16 |
| NL172053C (nl) | 1983-07-01 |
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