CA1068718A - Hydrogen end-capped fluorocarbon siloxane composition - Google Patents
Hydrogen end-capped fluorocarbon siloxane compositionInfo
- Publication number
- CA1068718A CA1068718A CA262,161A CA262161A CA1068718A CA 1068718 A CA1068718 A CA 1068718A CA 262161 A CA262161 A CA 262161A CA 1068718 A CA1068718 A CA 1068718A
- Authority
- CA
- Canada
- Prior art keywords
- siloxane
- fluorocarbon
- radical
- formula
- silicon
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 105
- -1 fluorocarbon siloxane Chemical class 0.000 title claims abstract description 73
- 229910052739 hydrogen Inorganic materials 0.000 title description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title description 4
- 239000001257 hydrogen Substances 0.000 title description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 50
- 239000003795 chemical substances by application Substances 0.000 claims description 31
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 31
- 229910052697 platinum Inorganic materials 0.000 claims description 25
- 239000003054 catalyst Substances 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 229920005603 alternating copolymer Polymers 0.000 claims description 7
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims description 3
- 239000008240 homogeneous mixture Substances 0.000 claims description 2
- 230000009973 reversion resistant effect Effects 0.000 abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229920002554 vinyl polymer Polymers 0.000 description 12
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 11
- 239000000377 silicon dioxide Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 10
- 229920001296 polysiloxane Polymers 0.000 description 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 8
- 239000000945 filler Substances 0.000 description 8
- 229910000077 silane Inorganic materials 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- JQZGUQIEPRIDMR-UHFFFAOYSA-N 3-methylbut-1-yn-1-ol Chemical compound CC(C)C#CO JQZGUQIEPRIDMR-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 239000003060 catalysis inhibitor Substances 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 239000003517 fume Substances 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920005604 random copolymer Polymers 0.000 description 3
- 230000003014 reinforcing effect Effects 0.000 description 3
- 238000010058 rubber compounding Methods 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000005739 1,1,2,2-tetrafluoroethanediyl group Chemical group FC(F)([*:1])C(F)(F)[*:2] 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000004965 Silica aerogel Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- BUMGIEFFCMBQDG-UHFFFAOYSA-N dichlorosilicon Chemical compound Cl[Si]Cl BUMGIEFFCMBQDG-UHFFFAOYSA-N 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000013536 elastomeric material Substances 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000013038 hand mixing Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000009987 spinning Methods 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
- C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/485—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms containing less than 25 silicon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0896—Compounds with a Si-H linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/14—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/647,473 US4057566A (en) | 1976-01-08 | 1976-01-08 | Fluorocarbon siloxane compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1068718A true CA1068718A (en) | 1979-12-25 |
Family
ID=24597136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA262,161A Expired CA1068718A (en) | 1976-01-08 | 1976-09-28 | Hydrogen end-capped fluorocarbon siloxane composition |
Country Status (6)
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4057566A (en) * | 1976-01-08 | 1977-11-08 | Dow Corning Corporation | Fluorocarbon siloxane compositions |
| JPS6030713B2 (ja) * | 1981-07-27 | 1985-07-18 | 東芝シリコ−ン株式会社 | 被覆用組成物および被覆方法 |
| US4488771A (en) * | 1982-03-08 | 1984-12-18 | Allied Corporation | Fluorosilicone elastomers, method of making such elastomers and electrical connectors including the elastomers |
| US4525528A (en) * | 1983-10-11 | 1985-06-25 | General Electric Company | Peroxide-curable fluorosilicone copolymer compositions |
| JPS60184724U (ja) * | 1984-05-21 | 1985-12-07 | 三菱自動車工業株式会社 | ４輪駆動・２輪駆動切換スイツチ付ギヤシフトノブ |
| US4565714B1 (en) * | 1984-06-14 | 1999-06-29 | Minnesota Mining & Mfg | Low surface energy material |
| JPH0514724Y2 (US20030220297A1-20031127-C00074.png) * | 1986-01-25 | 1993-04-20 | ||
| JPS6350733U (US20030220297A1-20031127-C00074.png) * | 1986-09-20 | 1988-04-06 | ||
| JPS63205359A (ja) * | 1987-02-20 | 1988-08-24 | Shin Etsu Chem Co Ltd | 硬化性フツ素シリコ−ン組成物 |
| JPH0162151U (US20030220297A1-20031127-C00074.png) * | 1987-10-16 | 1989-04-20 | ||
| US5082706A (en) * | 1988-11-23 | 1992-01-21 | Dow Corning Corporation | Pressure sensitive adhesive/release liner laminate |
| WO1990015098A1 (en) * | 1989-05-29 | 1990-12-13 | Kanegafuchi Chemical Industry Co., Ltd. | Curing agent, method of preparation thereof, and curable composition prepared therefrom |
| US5409995A (en) * | 1989-05-29 | 1995-04-25 | Kanegafuchi Chemical Industry Co., Ltd. | Curing agent, preparation thereof and curable composition comprising the same |
| JP2761931B2 (ja) * | 1989-08-10 | 1998-06-04 | 東レ・ダウコーニング・シリコーン株式会社 | オルガノポリシロキサン及びその製造方法 |
| DE69119980T2 (de) * | 1990-07-06 | 1997-02-13 | Shinetsu Chemical Co | Polysilethylensiloxan |
| JPH0786175B2 (ja) * | 1990-11-29 | 1995-09-20 | 信越化学工業株式会社 | 離型耐久性に優れたシリコーンゴム組成物 |
| US5342913A (en) * | 1990-11-29 | 1994-08-30 | Shin-Etsu Chemical Co., Ltd. | Silicon rubber composition having excellent durability in repeated mold release |
| JP2598340B2 (ja) * | 1991-01-24 | 1997-04-09 | 信越化学工業株式会社 | 水素シロキサンの製造方法 |
| JPH0751583B2 (ja) * | 1991-05-15 | 1995-06-05 | 信越化学工業株式会社 | 有機けい素化合物 |
| JPH0692482B2 (ja) * | 1991-06-27 | 1994-11-16 | 信越化学工業株式会社 | 有機けい素化合物 |
| DE69222819T2 (de) * | 1991-07-23 | 1998-05-28 | Shinetsu Chemical Co | Härtbare Siliconzusammensetzung |
| JP2619752B2 (ja) * | 1991-09-10 | 1997-06-11 | 信越化学工業株式会社 | 硬化性シリコーン組成物 |
| JP2619753B2 (ja) * | 1991-09-10 | 1997-06-11 | 信越化学工業株式会社 | 硬化性シリコーン組成物 |
| US5196558A (en) * | 1991-08-07 | 1993-03-23 | Shin-Etsu Chemical Company, Limited | Siloxane compounds |
| JPH0774222B2 (ja) * | 1991-12-24 | 1995-08-09 | 信越化学工業株式会社 | シロキサン化合物 |
| US5314981A (en) * | 1992-03-27 | 1994-05-24 | Shin-Etsu Chemical Co., Ltd. | Room temperature curable organopolysiloxane composition and cured product of the same |
| JP2701109B2 (ja) * | 1992-05-21 | 1998-01-21 | 信越化学工業株式会社 | 含フッ素有機ケイ素化合物 |
| US5264522A (en) * | 1992-09-10 | 1993-11-23 | Shin-Etsu Chemical Co., Ltd. | Heat-curable fluorosilicone rubber composition and cured product thereof |
| JP2954444B2 (ja) * | 1993-03-12 | 1999-09-27 | 信越化学工業株式会社 | 室温硬化性組成物 |
| JPH0770324A (ja) * | 1993-09-03 | 1995-03-14 | Toray Dow Corning Silicone Co Ltd | 有機ケイ素重合体の製造方法 |
| JPH0859839A (ja) * | 1994-08-18 | 1996-03-05 | Toray Dow Corning Silicone Co Ltd | 含フッ素有機ケイ素共重合体 |
| EP0725113B1 (en) * | 1995-01-23 | 2000-09-27 | Shin-Etsu Chemical Co., Ltd. | Fluorinated amide silicone compounds and curable siloxane compositions |
| JP3098932B2 (ja) * | 1995-05-12 | 2000-10-16 | 信越化学工業株式会社 | プライマー組成物 |
| EP0745604A3 (en) * | 1995-05-29 | 1998-07-29 | Shin-Etsu Chemical Co., Ltd. | Room temperature curable fluoropolymer composition; and fluorine-containing organosilicon compounds, a method of producing the same, and room temperature curable silicone composition containing the same |
| JP3239717B2 (ja) * | 1995-09-29 | 2001-12-17 | 信越化学工業株式会社 | 硬化性組成物 |
| EP1097958A1 (en) * | 1999-11-03 | 2001-05-09 | Daikin Industries, Limited | Fluoroelastomers for a wide temperature range of applications |
| CN100338108C (zh) * | 2002-03-14 | 2007-09-19 | 大金工业株式会社 | 含氟共聚物、含氟共聚物制造方法、含氟共聚物固化用组合物和固化物 |
| JP4618230B2 (ja) * | 2002-12-05 | 2011-01-26 | ダイキン工業株式会社 | 含フッ素ポリマー組成物及び硬化体 |
| WO2004050758A1 (ja) * | 2002-12-05 | 2004-06-17 | Daikin Industries, Ltd. | 含フッ素ポリマー組成物及び硬化体 |
| JP4098699B2 (ja) * | 2003-10-23 | 2008-06-11 | 信越化学工業株式会社 | 硬化性パーフルオロポリエ−テル系組成物 |
| US20060240248A1 (en) * | 2005-04-26 | 2006-10-26 | Canon Kabushiki Kaisha | Electrophotographic belt, electrophotographic apparatus, process for producing the electrophotographic belt, and intermediate transfer belt |
| US7872053B2 (en) * | 2007-03-26 | 2011-01-18 | Momentive Performance Materials GmbH & Co., KG | Surface active organosilicone compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL126403C (US20030220297A1-20031127-C00074.png) * | 1963-10-07 | 1900-01-01 | ||
| US3398177A (en) * | 1965-05-10 | 1968-08-20 | Dow Corning | Redistribution of sih bonds |
| US3542830A (en) * | 1968-08-02 | 1970-11-24 | Dow Corning | Fluorocarbon silicone compositions |
| US3989667A (en) * | 1974-12-02 | 1976-11-02 | Dow Corning Corporation | Olefinic siloxanes as platinum inhibitors |
| US3975362A (en) * | 1975-04-28 | 1976-08-17 | Dow Corning Corporation | Low temperature reversion resistant organosilicon polymers |
| US4057566A (en) * | 1976-01-08 | 1977-11-08 | Dow Corning Corporation | Fluorocarbon siloxane compositions |
-
1976
- 1976-01-08 US US05/647,473 patent/US4057566A/en not_active Expired - Lifetime
- 1976-09-28 CA CA262,161A patent/CA1068718A/en not_active Expired
- 1976-10-25 DE DE2648242A patent/DE2648242C2/de not_active Expired
- 1976-11-26 JP JP14208176A patent/JPS5285123A/ja active Granted
- 1976-12-31 GB GB54476/76A patent/GB1575416A/en not_active Expired
-
1977
- 1977-01-06 FR FR7700238A patent/FR2337731A1/fr active Granted
- 1977-06-03 US US05/803,110 patent/US4100136A/en not_active Expired - Lifetime
-
1980
- 1980-05-08 JP JP55060010A patent/JPS5856582B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5285123A (en) | 1977-07-15 |
| JPS5725037B2 (US20030220297A1-20031127-C00074.png) | 1982-05-27 |
| JPS5856582B2 (ja) | 1983-12-15 |
| DE2648242C2 (de) | 1982-12-09 |
| JPS56829A (en) | 1981-01-07 |
| US4057566A (en) | 1977-11-08 |
| US4100136A (en) | 1978-07-11 |
| DE2648242A1 (de) | 1977-08-25 |
| GB1575416A (en) | 1980-09-24 |
| FR2337731B1 (US20030220297A1-20031127-C00074.png) | 1980-03-14 |
| FR2337731A1 (fr) | 1977-08-05 |
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