DE2618852C2 - Verfahren zum Herstellen von Diorganopolysiloxan-Copolymeren - Google Patents
Verfahren zum Herstellen von Diorganopolysiloxan-CopolymerenInfo
- Publication number
- DE2618852C2 DE2618852C2 DE2618852A DE2618852A DE2618852C2 DE 2618852 C2 DE2618852 C2 DE 2618852C2 DE 2618852 A DE2618852 A DE 2618852A DE 2618852 A DE2618852 A DE 2618852A DE 2618852 C2 DE2618852 C2 DE 2618852C2
- Authority
- DE
- Germany
- Prior art keywords
- cyclic
- mixture
- copolymers
- copolymer
- catalyst
- 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
- 238000000034 method Methods 0.000 title description 20
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 title description 7
- 229920001577 copolymer Polymers 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 4
- -1 polysiloxane Polymers 0.000 description 25
- 125000004122 cyclic group Chemical group 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000010 aprotic solvent Substances 0.000 description 9
- 229920001971 elastomer Polymers 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 229920001296 polysiloxane Polymers 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000005060 rubber Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000013638 trimer Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Chemical group 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VCYDUTCMKSROID-UHFFFAOYSA-N 2,2,4,4,6,6-hexakis-phenyl-1,3,5,2,4,6-trioxatrisilinane Chemical compound O1[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si]1(C=1C=CC=CC=1)C1=CC=CC=C1 VCYDUTCMKSROID-UHFFFAOYSA-N 0.000 description 1
- VLQZJOLYNOGECD-UHFFFAOYSA-N 2,4,6-trimethyl-1,3,5,2,4,6-trioxatrisilinane Chemical compound C[SiH]1O[SiH](C)O[SiH](C)O1 VLQZJOLYNOGECD-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- KQNZLOUWXSAZGD-UHFFFAOYSA-N benzylperoxymethylbenzene Chemical compound C=1C=CC=CC=1COOCC1=CC=CC=C1 KQNZLOUWXSAZGD-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 235000021190 leftovers Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/574,331 US3974120A (en) | 1975-05-05 | 1975-05-05 | Fluorosilicone copolymers and process for the preparation thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2618852A1 DE2618852A1 (de) | 1976-11-18 |
| DE2618852C2 true DE2618852C2 (de) | 1984-10-04 |
Family
ID=24295654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2618852A Expired DE2618852C2 (de) | 1975-05-05 | 1976-04-29 | Verfahren zum Herstellen von Diorganopolysiloxan-Copolymeren |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3974120A (enExample) |
| JP (1) | JPS51134796A (enExample) |
| DE (1) | DE2618852C2 (enExample) |
| FR (1) | FR2310373A1 (enExample) |
| GB (1) | GB1540876A (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4089833A (en) * | 1977-05-02 | 1978-05-16 | General Electric Company | Process aids for fluorosilicone polymers |
| US4317899A (en) * | 1978-11-13 | 1982-03-02 | General Electric Company | Process for producing fluorosilicone polymers |
| JPS5628219A (en) * | 1979-08-17 | 1981-03-19 | Asahi Glass Co Ltd | New fluorine-containing elastomer |
| US4348531A (en) * | 1979-08-30 | 1982-09-07 | General Electric Company | Fluorosilicone polydimethylsiloxane equilibration chainstopper and process for manufacture |
| GB2057477B (en) * | 1979-08-30 | 1983-10-26 | Gen Electric | Dimethylsiloxane-methylfluoroalkylsiloxane copolymers |
| US4287353A (en) * | 1979-11-09 | 1981-09-01 | General Electric Company | Process for synthesizing silanol chain-stopped fluorosiloxane fluids |
| US4355121A (en) * | 1981-04-09 | 1982-10-19 | General Electric Company | Heat strength curable silicone rubber compositions |
| US4499229A (en) * | 1983-04-01 | 1985-02-12 | General Electric Company | One package, stable, moisture curable, alkoxy-terminated organopolysiloxane compositions |
| US4683277A (en) * | 1986-07-02 | 1987-07-28 | Dow Corning Corporation | Method for preparing vinyl terminated fluorine-containing polydiorganosiloxane |
| US5140087A (en) * | 1988-04-22 | 1992-08-18 | Chisso Corporation | Organosiloxane and process for preparing the same |
| JP2538308B2 (ja) * | 1988-04-22 | 1996-09-25 | チッソ株式会社 | オルガノシロキサン |
| GB8917329D0 (en) * | 1989-07-28 | 1989-09-13 | Dow Corning | Silethynylsiloxane copolymers and method of making them |
| US4977290A (en) * | 1989-11-20 | 1990-12-11 | General Electric Company | Polar aprotic catalysts for formation of fluorosilicone fluids |
| US5079291A (en) * | 1989-11-20 | 1992-01-07 | General Electric Company | Polar aprotic catalysts for formation of fluorosilicone fluids |
| JPH05279481A (ja) * | 1992-03-31 | 1993-10-26 | Toray Dow Corning Silicone Co Ltd | フルオロシリコ−ンブロック共重合体およびその製造方法 |
| WO1994005749A1 (en) * | 1992-09-09 | 1994-03-17 | Lord Corporation | High strength, low conductivity electrorheological materials |
| JPH07216233A (ja) * | 1992-09-21 | 1995-08-15 | Toray Dow Corning Silicone Co Ltd | フルオロシリコーンゴム組成物 |
| GB2278846B (en) * | 1993-06-10 | 1997-04-16 | Gen Electric | Fluorosilicone terpolymeric fluid |
| US5696219A (en) * | 1997-01-21 | 1997-12-09 | Dow Corning Corporation | Silyl ester initiators for cyclosiloxane ring opening polymerization |
| US5830969A (en) * | 1997-05-28 | 1998-11-03 | Dow Corning Corporation | Silyl ester initiators for ring opening polymerization of cyclosiloxanes |
| US5853617A (en) * | 1997-05-14 | 1998-12-29 | Gallagher; Christopher T. | Method and composition for suppressing oil-based foams |
| US6056976A (en) * | 1998-11-12 | 2000-05-02 | Leiras Oy | Elastomer, its preparation and use |
| EP1681313A1 (en) | 2005-01-17 | 2006-07-19 | DSM IP Assets B.V. | Heat stabilized moulding composition |
| US20080167390A1 (en) * | 2006-06-01 | 2008-07-10 | James Archer | Defoamer composition for suppressing oil-based and water-based foams |
| US7799888B2 (en) * | 2007-04-27 | 2010-09-21 | Gelest, Inc. | Low molecular weight siloxanes with one functional group |
| JP5338380B2 (ja) * | 2008-12-02 | 2013-11-13 | 信越化学工業株式会社 | オルガノポリシロキサン及びその製造方法並びにフルオロシリコーンゴム組成物 |
| JP5278242B2 (ja) * | 2009-08-14 | 2013-09-04 | 信越化学工業株式会社 | 分子鎖両末端トリオルガノシロキシ基封鎖オルガノポリシロキサンの製造方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1226739A (fr) * | 1958-04-07 | 1960-07-15 | Dow Corning | Fluides fluoroalkylsiloxanes |
| US3122521A (en) * | 1960-03-18 | 1964-02-25 | Dow Corning | Method of polymerizing fluoroalkyl-substituted cyclotrisiloxanes |
| DE1495501B2 (de) * | 1963-03-25 | 1971-11-18 | Dow Corning Corp , Midland, Mich (V St A ) | Polymerisationskatalysatoren fuer cyclische organosilicium verbindungen |
| US3249585A (en) * | 1964-04-29 | 1966-05-03 | Dow Corning | Preparation of siloxanes with sih bonds with an alkyl lithium catalyst |
| US3483270A (en) * | 1966-04-11 | 1969-12-09 | Gen Electric | Stereospecific organosiloxane-macromolecular hydrocarbon block copolymers |
| US3503926A (en) * | 1968-05-17 | 1970-03-31 | Dow Corning | Solid lubricant composition |
| BE756725A (fr) * | 1969-09-29 | 1971-03-29 | Dow Corning | Procede de preparation de 3,3,3-trifluoropropylmethylpolysiloxanes |
-
1975
- 1975-05-05 US US05/574,331 patent/US3974120A/en not_active Expired - Lifetime
-
1976
- 1976-04-29 DE DE2618852A patent/DE2618852C2/de not_active Expired
- 1976-04-30 GB GB17646/76A patent/GB1540876A/en not_active Expired
- 1976-05-04 JP JP51050044A patent/JPS51134796A/ja active Granted
- 1976-05-05 FR FR7613331A patent/FR2310373A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2310373A1 (fr) | 1976-12-03 |
| US3974120A (en) | 1976-08-10 |
| JPS618095B2 (enExample) | 1986-03-12 |
| DE2618852A1 (de) | 1976-11-18 |
| GB1540876A (en) | 1979-02-21 |
| FR2310373B1 (enExample) | 1981-08-21 |
| JPS51134796A (en) | 1976-11-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8125 | Change of the main classification |
Ipc: C08G 77/24 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |