DE2015249A1 - Blockcopolymerisate und Verfahren zu ihrer Herstellung - Google Patents
Blockcopolymerisate und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2015249A1 DE2015249A1 DE19702015249 DE2015249A DE2015249A1 DE 2015249 A1 DE2015249 A1 DE 2015249A1 DE 19702015249 DE19702015249 DE 19702015249 DE 2015249 A DE2015249 A DE 2015249A DE 2015249 A1 DE2015249 A1 DE 2015249A1
- Authority
- DE
- Germany
- Prior art keywords
- block
- styrene
- polymer
- copolymer
- conjugated diene
- 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.)
- Pending
Links
- 229920001400 block copolymer Polymers 0.000 title claims description 51
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 48
- 229920000642 polymer Polymers 0.000 claims description 47
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 29
- 229920001577 copolymer Polymers 0.000 claims description 27
- 150000001993 dienes Chemical class 0.000 claims description 26
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 12
- 238000009826 distribution Methods 0.000 claims description 11
- 239000007822 coupling agent Substances 0.000 claims description 9
- 238000005984 hydrogenation reaction Methods 0.000 claims description 9
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- 229920002857 polybutadiene Polymers 0.000 claims description 5
- 239000004711 α-olefin Substances 0.000 claims description 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 4
- 239000005062 Polybutadiene Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229920001195 polyisoprene Polymers 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 230000001588 bifunctional effect Effects 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 3
- 229930195733 hydrocarbon Natural products 0.000 claims 3
- 150000002430 hydrocarbons Chemical class 0.000 claims 3
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- -1 lithium alkyl compound Chemical class 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 229910001416 lithium ion Inorganic materials 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 2
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- SEQRDAAUNCRFIT-UHFFFAOYSA-N 1,1-dichlorobutane Chemical compound CCCC(Cl)Cl SEQRDAAUNCRFIT-UHFFFAOYSA-N 0.000 description 1
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229920001744 Polyaldehyde Polymers 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 150000005690 diesters Chemical group 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- BONOXOHRDYVMPV-UHFFFAOYSA-N lithium;prop-1-en-2-ylbenzene Chemical compound [Li].CC(=C)C1=CC=CC=C1 BONOXOHRDYVMPV-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005474 octanoate group Chemical group 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C08G81/021—Block or graft polymers containing only sequences of polymers of C08C or C08F
- C08G81/022—Block or graft polymers containing only sequences of polymers of C08C or C08F containing sequences of polymers of conjugated dienes and of polymers of alkenyl aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
- C08F297/04—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes
- C08F297/044—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes using a coupling agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/04—Reduction, e.g. hydrogenation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US81237569A | 1969-04-01 | 1969-04-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2015249A1 true DE2015249A1 (de) | 1970-10-08 |
Family
ID=25209381
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19702015249 Pending DE2015249A1 (de) | 1969-04-01 | 1970-03-31 | Blockcopolymerisate und Verfahren zu ihrer Herstellung |
Country Status (6)
Country | Link |
---|---|
AU (1) | AU1317570A (en, 2012) |
BE (1) | BE747591A (en, 2012) |
DE (1) | DE2015249A1 (en, 2012) |
FR (1) | FR2042247A5 (en, 2012) |
GB (1) | GB1264741A (en, 2012) |
NL (1) | NL7004513A (en, 2012) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4954490A (en, 2012) * | 1972-09-29 | 1974-05-27 | ||
DE2535801A1 (de) * | 1974-09-03 | 1976-03-11 | Goodyear Tire & Rubber | Verfahren zur herstellung eines thermoplastischen blockpolymeren |
EP0014947A1 (en) * | 1979-02-15 | 1980-09-03 | The Dow Chemical Company | Block copolymers of diene having their terminal end blocks of a random copolymer of styrene or alkylstyrene and an alpha-methylstyrene, and their preparation |
EP0118572A1 (en) * | 1981-03-27 | 1984-09-19 | The Dow Chemical Company | A process for preparation of diene styrene alpha-methylstyrene block polymers and polymers therefrom |
EP0135168A3 (en) * | 1983-08-22 | 1986-08-27 | The Dow Chemical Company | A process for preparation of copolymers of isopropenyl aromatic monomer and vinyl aromatic monomer |
WO1994015997A1 (en) * | 1993-01-08 | 1994-07-21 | The Dow Chemical Company | High-strength films of block copolymer latices |
US5556911A (en) * | 1994-11-15 | 1996-09-17 | The Dow Chemical Company | Films from aqueous dispersions of block copolymers having hydrogenated conjugated diene block |
US5563204A (en) * | 1993-01-08 | 1996-10-08 | The Dow Chemical Company | High-strength films of block copolymer latices |
US5578674A (en) * | 1993-01-08 | 1996-11-26 | The Dow Chemical Company | High-strength films of block copolymer latices |
US5905097A (en) * | 1993-01-08 | 1999-05-18 | The Dow Chemical Company | High-strength breathable films of block copolymer lattices |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3912793A (en) * | 1972-09-29 | 1975-10-14 | Denki Kagaku Kogyo Kk | Block copolymers and process for the preparation thereof |
JPS533791B2 (en, 2012) | 1974-05-15 | 1978-02-09 | ||
US4427837A (en) | 1981-03-27 | 1984-01-24 | The Dow Chemical Company | Process for preparation of diene-styrene-α-methylstyrene block polymers and polymers therefrom |
IT1186752B (it) * | 1985-07-10 | 1987-12-16 | Eniricerche Spa | Copolimeri a blocchi idrogenati e loro processo di sintesi |
EP0719833A3 (en) | 1994-12-30 | 1997-01-15 | Gen Electric | Thermoplastic compositions containing polyether phenylene resins and polyolefins |
US6221283B1 (en) | 1999-05-07 | 2001-04-24 | General Electric Company | Conductive compositions with compositionally controlled bulk resistivity |
US6469093B1 (en) | 1999-11-12 | 2002-10-22 | General Electric Company | Conductive polyphenylene ether-polyamide blend |
EP1280858A1 (en) | 2000-05-04 | 2003-02-05 | General Electric Company | Method for improving the paint adhesion of compatibilized polyphenylene ether-polyamide compositions |
WO2002015302A2 (en) * | 2000-08-14 | 2002-02-21 | World Properties Inc. | Thermosetting composition for electrochemical cell components and methods of making thereof |
US6500895B1 (en) | 2000-10-13 | 2002-12-31 | General Electric Company | Thermoplastic blend comprising poly(arylene ether) and polyamide |
US6353050B1 (en) | 2000-10-13 | 2002-03-05 | General Electric Co. | Thermoplastic blend comprising poly(arylene ether) and polyamide |
US6583205B2 (en) | 2001-05-07 | 2003-06-24 | General Electric Company | Flame retardant expandable poly(arylene ether)/polystyrene compositions and preparation thereof |
US6630527B2 (en) | 2001-10-19 | 2003-10-07 | General Electric Company | UV stabilized, impact modified polyester/polycarbonate blends, articles, and methods of manufacture thereof |
US8034870B2 (en) | 2003-12-17 | 2011-10-11 | Sabic Innovative Plastics Ip B.V. | Flame-retardant polyester composition |
US7037986B2 (en) | 2003-12-19 | 2006-05-02 | General Electric Company | Lead free solder friendly thermoplastic blends and methods of manufacture thereof |
US7947204B2 (en) | 2004-04-16 | 2011-05-24 | Sabic Innovative Plastics Ip B.V. | Poly(arylene ether) compression molding |
US7212110B1 (en) | 2004-04-19 | 2007-05-01 | Advanced Neuromodulation Systems, Inc. | Implantable device and system and method for wireless communication |
US7825176B2 (en) | 2005-08-31 | 2010-11-02 | Sabic Innovative Plastics Ip B.V. | High flow polyester composition |
BRPI0709865B1 (pt) * | 2006-03-24 | 2018-05-29 | Kraton Polymers U.S. Llc | Processo para a preparação de copolímeros em bloco, copolímero em bloco, e, composição elastomérica |
US7612130B2 (en) | 2006-10-16 | 2009-11-03 | Sabic Innovative Plastics Ip B.V. | Composition of polyester, aromatic epoxy compound and epoxy-functional polyolefin and/or copolyester |
US7868090B2 (en) | 2006-12-28 | 2011-01-11 | Sabic Innovative Plastics Ip B.V. | Polyester molding compositions |
US8222347B2 (en) | 2007-07-25 | 2012-07-17 | Sabic Innovative Plastics Ip B.V. | Polyester-polycarbonate compositions |
US7915328B2 (en) | 2008-12-30 | 2011-03-29 | Sabic Innovative Plastics Ip B.V. | Flame retardant resinous compositions and process |
US7915329B2 (en) | 2008-12-30 | 2011-03-29 | Sabic Innovative Plastics Ip B.V. | Flame retardant resinous compositions and process |
CN107109008A (zh) | 2014-12-05 | 2017-08-29 | Sabic环球技术有限责任公司 | 阻燃性聚苯乙烯组合物 |
CN116888533A (zh) | 2021-02-25 | 2023-10-13 | 巴斯夫欧洲公司 | 用于涂敷、2d物体形成和3d打印的包含可光聚合液体和环氧前体的可固化组合物 |
-
1970
- 1970-03-19 BE BE747591D patent/BE747591A/xx unknown
- 1970-03-31 NL NL7004513A patent/NL7004513A/xx unknown
- 1970-03-31 DE DE19702015249 patent/DE2015249A1/de active Pending
- 1970-03-31 AU AU13175/70A patent/AU1317570A/en not_active Expired
- 1970-03-31 GB GB1264741D patent/GB1264741A/en not_active Expired
- 1970-03-31 FR FR7011404A patent/FR2042247A5/fr not_active Expired
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4954490A (en, 2012) * | 1972-09-29 | 1974-05-27 | ||
DE2535801A1 (de) * | 1974-09-03 | 1976-03-11 | Goodyear Tire & Rubber | Verfahren zur herstellung eines thermoplastischen blockpolymeren |
EP0014947A1 (en) * | 1979-02-15 | 1980-09-03 | The Dow Chemical Company | Block copolymers of diene having their terminal end blocks of a random copolymer of styrene or alkylstyrene and an alpha-methylstyrene, and their preparation |
EP0118572A1 (en) * | 1981-03-27 | 1984-09-19 | The Dow Chemical Company | A process for preparation of diene styrene alpha-methylstyrene block polymers and polymers therefrom |
EP0135168A3 (en) * | 1983-08-22 | 1986-08-27 | The Dow Chemical Company | A process for preparation of copolymers of isopropenyl aromatic monomer and vinyl aromatic monomer |
WO1994015997A1 (en) * | 1993-01-08 | 1994-07-21 | The Dow Chemical Company | High-strength films of block copolymer latices |
US5563204A (en) * | 1993-01-08 | 1996-10-08 | The Dow Chemical Company | High-strength films of block copolymer latices |
US5578674A (en) * | 1993-01-08 | 1996-11-26 | The Dow Chemical Company | High-strength films of block copolymer latices |
US5905097A (en) * | 1993-01-08 | 1999-05-18 | The Dow Chemical Company | High-strength breathable films of block copolymer lattices |
US5556911A (en) * | 1994-11-15 | 1996-09-17 | The Dow Chemical Company | Films from aqueous dispersions of block copolymers having hydrogenated conjugated diene block |
US5567760A (en) * | 1994-11-15 | 1996-10-22 | The Dow Chemical Company | Films from aqueous dispersions of block copolymers having hydrogenated conjugated diene block |
Also Published As
Publication number | Publication date |
---|---|
GB1264741A (en, 2012) | 1972-02-23 |
FR2042247A5 (en, 2012) | 1971-02-05 |
AU1317570A (en) | 1971-10-17 |
NL7004513A (en, 2012) | 1970-10-05 |
BE747591A (fr) | 1970-09-21 |
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