DE1230209B - Thermoplastische Massen zur Herstellung schwerentflammbarer Formteile aus Polyolefinen - Google Patents
Thermoplastische Massen zur Herstellung schwerentflammbarer Formteile aus PolyolefinenInfo
- Publication number
- DE1230209B DE1230209B DEC30334A DEC0030334A DE1230209B DE 1230209 B DE1230209 B DE 1230209B DE C30334 A DEC30334 A DE C30334A DE C0030334 A DEC0030334 A DE C0030334A DE 1230209 B DE1230209 B DE 1230209B
- Authority
- DE
- Germany
- Prior art keywords
- flame
- polyolefins
- aromatic
- weight
- percent
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 18
- 229920000098 polyolefin Polymers 0.000 title claims description 18
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims description 11
- 239000003063 flame retardant Substances 0.000 title claims description 11
- 229920001169 thermoplastic Polymers 0.000 title claims description 4
- 239000004416 thermosoftening plastic Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 20
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 239000012188 paraffin wax Substances 0.000 claims description 12
- 125000001246 bromo group Chemical group Br* 0.000 claims description 10
- -1 polyethylene Polymers 0.000 description 23
- 239000000463 material Substances 0.000 description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
- 229910052794 bromium Inorganic materials 0.000 description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 239000004698 Polyethylene Substances 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 229920000573 polyethylene Polymers 0.000 description 9
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 8
- 239000004743 Polypropylene Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000026030 halogenation Effects 0.000 description 5
- 238000005658 halogenation reaction Methods 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- GVPODVKBTHCGFU-UHFFFAOYSA-N 2,4,6-tribromoaniline Chemical compound NC1=C(Br)C=C(Br)C=C1Br GVPODVKBTHCGFU-UHFFFAOYSA-N 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 2
- QFFSHOBJNKBNCQ-UHFFFAOYSA-N 2,2,2-tribromo-n-phenylacetamide Chemical compound BrC(Br)(Br)C(=O)NC1=CC=CC=C1 QFFSHOBJNKBNCQ-UHFFFAOYSA-N 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- LJDGJCNHVGGOFW-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-(2-bromophenoxy)benzene Chemical compound BrC1=CC=CC=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br LJDGJCNHVGGOFW-UHFFFAOYSA-N 0.000 description 1
- ACRQLFSHISNWRY-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-phenoxybenzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=CC=CC=C1 ACRQLFSHISNWRY-UHFFFAOYSA-N 0.000 description 1
- VIHUMJGEWQPWOT-UHFFFAOYSA-N 1,2,3-tribromo-4-(3-bromophenoxy)benzene Chemical compound BrC1=CC=CC(OC=2C(=C(Br)C(Br)=CC=2)Br)=C1 VIHUMJGEWQPWOT-UHFFFAOYSA-N 0.000 description 1
- PKQYSCBUFZOAPE-UHFFFAOYSA-N 1,2-dibenzyl-3-methylbenzene Chemical compound C=1C=CC=CC=1CC=1C(C)=CC=CC=1CC1=CC=CC=C1 PKQYSCBUFZOAPE-UHFFFAOYSA-N 0.000 description 1
- BUQBQEYUVAKJQK-UHFFFAOYSA-N 1,2-dibromo-4-(2-bromophenoxy)benzene Chemical compound C1=C(Br)C(Br)=CC=C1OC1=CC=CC=C1Br BUQBQEYUVAKJQK-UHFFFAOYSA-N 0.000 description 1
- HRICYCBIRUKDED-UHFFFAOYSA-N 1-benzyl-2-(2-phenylethyl)benzene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1CC1=CC=CC=C1 HRICYCBIRUKDED-UHFFFAOYSA-N 0.000 description 1
- BUZMJVBOGDBMGI-UHFFFAOYSA-N 1-phenylpropylbenzene Chemical compound C=1C=CC=CC=1C(CC)C1=CC=CC=C1 BUZMJVBOGDBMGI-UHFFFAOYSA-N 0.000 description 1
- JPSLMXXHRJKETL-UHFFFAOYSA-N 2,3,4-tribromo-5,6-dichlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Br)C(Br)=C1Br JPSLMXXHRJKETL-UHFFFAOYSA-N 0.000 description 1
- KREAPORYQICDAC-UHFFFAOYSA-N 2,3,5-tribromo-4-chlorophenol Chemical compound BrC=1C(=C(C(=C(C=1)O)Br)Br)Cl KREAPORYQICDAC-UHFFFAOYSA-N 0.000 description 1
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- VMVGVGMRBKYIGN-UHFFFAOYSA-N n-naphthalen-1-ylnaphthalen-1-amine Chemical compound C1=CC=C2C(NC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 VMVGVGMRBKYIGN-UHFFFAOYSA-N 0.000 description 1
- UNJZLNFHHINVOB-UHFFFAOYSA-N n-naphthalen-1-ylnaphthalen-2-amine Chemical compound C1=CC=C2C(NC=3C=C4C=CC=CC4=CC=3)=CC=CC2=C1 UNJZLNFHHINVOB-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/02—Halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/02—Halogenated hydrocarbons
- C08K5/03—Halogenated hydrocarbons aromatic, e.g. C6H5-CH2-Cl
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL302817D NL302817A (enrdf_load_stackoverflow) | 1963-07-03 | ||
| NL135465D NL135465C (enrdf_load_stackoverflow) | 1963-07-03 | ||
| DEC30334A DE1230209B (de) | 1963-07-03 | 1963-07-03 | Thermoplastische Massen zur Herstellung schwerentflammbarer Formteile aus Polyolefinen |
| DE1963C0031274 DE1253452B (de) | 1963-07-03 | 1963-10-30 | Thermoplastische Massen zur Herstellung schwerentflammbarer Formteile aus Polyolefinen |
| SE105064A SE311750B (enrdf_load_stackoverflow) | 1963-07-03 | 1964-01-28 | |
| CH344764A CH441748A (de) | 1963-07-03 | 1964-03-18 | Schwerentflammbare Polyolefin-Mischungen |
| FR978840A FR1399195A (fr) | 1963-07-03 | 1964-06-19 | Mélanges de polyoléfines difficilement inflammables |
| AT571264A AT253773B (de) | 1963-07-03 | 1964-07-02 | Schwerentflammbare Polyolefin-Mischungen |
| GB2730264A GB1062740A (en) | 1963-07-03 | 1964-07-02 | Self-extinguishing polyolefine mixtures |
| FR992394A FR86638E (fr) | 1963-07-03 | 1964-10-23 | Mélanges de polyoléfines difficilement inflammables |
| CH1389964A CH435725A (de) | 1963-07-03 | 1964-10-27 | Schwerentflammbare Polyolefin-Mischungen |
| GB4411164A GB1076608A (en) | 1963-07-03 | 1964-10-29 | Self-extinguishing polyolefine mixtures |
| NL6412657A NL6412657A (enrdf_load_stackoverflow) | 1963-07-03 | 1964-10-30 | |
| FR9723A FR87565E (fr) | 1963-07-03 | 1965-03-18 | Mélanges de polyoléfines difficilement inflammables |
| GB12858/65A GB1093101A (en) | 1963-07-03 | 1965-03-26 | Self-extinguishing polyolefine mixtures |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC30334A DE1230209B (de) | 1963-07-03 | 1963-07-03 | Thermoplastische Massen zur Herstellung schwerentflammbarer Formteile aus Polyolefinen |
| DE1963C0031274 DE1253452B (de) | 1963-07-03 | 1963-10-30 | Thermoplastische Massen zur Herstellung schwerentflammbarer Formteile aus Polyolefinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1230209B true DE1230209B (de) | 1966-12-08 |
Family
ID=25969699
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC30334A Pending DE1230209B (de) | 1963-07-03 | 1963-07-03 | Thermoplastische Massen zur Herstellung schwerentflammbarer Formteile aus Polyolefinen |
| DE1963C0031274 Pending DE1253452B (de) | 1963-07-03 | 1963-10-30 | Thermoplastische Massen zur Herstellung schwerentflammbarer Formteile aus Polyolefinen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1963C0031274 Pending DE1253452B (de) | 1963-07-03 | 1963-10-30 | Thermoplastische Massen zur Herstellung schwerentflammbarer Formteile aus Polyolefinen |
Country Status (5)
| Country | Link |
|---|---|
| CH (2) | CH441748A (enrdf_load_stackoverflow) |
| DE (2) | DE1230209B (enrdf_load_stackoverflow) |
| GB (2) | GB1062740A (enrdf_load_stackoverflow) |
| NL (3) | NL6412657A (enrdf_load_stackoverflow) |
| SE (1) | SE311750B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3214416A1 (de) * | 1982-04-20 | 1983-10-27 | Chemische Fabrik Kalk GmbH, 5000 Köln | Tetrakis-(brommethyl)-diphenylaether, verfahren zu seiner herstellung und seine verwendung als brandschutzmittel |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4032315A1 (de) * | 1990-10-11 | 1992-04-16 | Alveo Ag | Flammschutz-formulierung fuer organische polymere und ihre verwendung zur herstellung von brandfesten polyolefin-zusammensetzungen |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1103020B (de) * | 1959-02-04 | 1961-03-23 | Huels Chemische Werke Ag | Schwer entflammbare Formmasse auf Basis von Polyolefinen |
| DE1123823B (de) * | 1959-12-18 | 1962-02-15 | Huels Chemische Werke Ag | Schwer entflammbare Formmassen auf Basis von Polyolefinen |
| DE1135653B (de) * | 1960-07-25 | 1962-08-30 | Huels Chemische Werke Ag | Schwer entflammbare Formmassen aus Polyolefinen |
| DE1139636B (de) * | 1960-05-24 | 1962-11-15 | Hoechst Ag | Verfahren zum Flammfestmaschen von polymeren Monoolefinen oder polymeren Styrolen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL127537C (enrdf_load_stackoverflow) * | 1963-05-21 |
-
0
- NL NL302817D patent/NL302817A/xx unknown
- NL NL135465D patent/NL135465C/xx active
-
1963
- 1963-07-03 DE DEC30334A patent/DE1230209B/de active Pending
- 1963-10-30 DE DE1963C0031274 patent/DE1253452B/de active Pending
-
1964
- 1964-01-28 SE SE105064A patent/SE311750B/xx unknown
- 1964-03-18 CH CH344764A patent/CH441748A/de unknown
- 1964-07-02 GB GB2730264A patent/GB1062740A/en not_active Expired
- 1964-10-27 CH CH1389964A patent/CH435725A/de unknown
- 1964-10-29 GB GB4411164A patent/GB1076608A/en not_active Expired
- 1964-10-30 NL NL6412657A patent/NL6412657A/xx unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1103020B (de) * | 1959-02-04 | 1961-03-23 | Huels Chemische Werke Ag | Schwer entflammbare Formmasse auf Basis von Polyolefinen |
| DE1123823B (de) * | 1959-12-18 | 1962-02-15 | Huels Chemische Werke Ag | Schwer entflammbare Formmassen auf Basis von Polyolefinen |
| DE1139636B (de) * | 1960-05-24 | 1962-11-15 | Hoechst Ag | Verfahren zum Flammfestmaschen von polymeren Monoolefinen oder polymeren Styrolen |
| DE1135653B (de) * | 1960-07-25 | 1962-08-30 | Huels Chemische Werke Ag | Schwer entflammbare Formmassen aus Polyolefinen |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3214416A1 (de) * | 1982-04-20 | 1983-10-27 | Chemische Fabrik Kalk GmbH, 5000 Köln | Tetrakis-(brommethyl)-diphenylaether, verfahren zu seiner herstellung und seine verwendung als brandschutzmittel |
Also Published As
| Publication number | Publication date |
|---|---|
| CH441748A (de) | 1967-08-15 |
| NL135465C (enrdf_load_stackoverflow) | |
| DE1253452B (de) | 1967-11-02 |
| NL302817A (enrdf_load_stackoverflow) | |
| NL6412657A (enrdf_load_stackoverflow) | 1965-11-25 |
| GB1076608A (en) | 1967-07-19 |
| GB1062740A (en) | 1967-03-22 |
| SE311750B (enrdf_load_stackoverflow) | 1969-06-23 |
| CH435725A (de) | 1967-05-15 |
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