GB912203A - Mixed polycarbonate-polycarboxylic acid esters - Google Patents
Mixed polycarbonate-polycarboxylic acid estersInfo
- Publication number
- GB912203A GB912203A GB35031/61A GB3503161A GB912203A GB 912203 A GB912203 A GB 912203A GB 35031/61 A GB35031/61 A GB 35031/61A GB 3503161 A GB3503161 A GB 3503161A GB 912203 A GB912203 A GB 912203A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- phenol
- polyester
- glycol
- phosgene
- 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
- 239000002253 acid Substances 0.000 title 1
- 150000002148 esters Chemical class 0.000 title 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 8
- 229920000728 polyester Polymers 0.000 abstract 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 abstract 3
- 229920000642 polymer Polymers 0.000 abstract 3
- 229930185605 Bisphenol Natural products 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229920001577 copolymer Polymers 0.000 abstract 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 abstract 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 abstract 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 1
- XMUZQOKACOLCSS-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC=C1CO XMUZQOKACOLCSS-UHFFFAOYSA-N 0.000 abstract 1
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000011 acetone peroxide Substances 0.000 abstract 1
- 235000019401 acetone peroxide Nutrition 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 239000012772 electrical insulation material Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 abstract 1
- 238000000465 moulding Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 238000004382 potting Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 abstract 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
- C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
- C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/22—General preparatory processes using carbonyl halides
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/26—General preparatory processes using halocarbonates
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/26—General preparatory processes using halocarbonates
- C08G64/263—General preparatory processes using halocarbonates and cyclic ethers
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/44—Polyester-amides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/06—Unsaturated polyesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
- Epoxy Resins (AREA)
- Reinforced Plastic Materials (AREA)
- Developing Agents For Electrophotography (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Copolymers containing both carbonate and carboxylate linkage are made by reacting a hydroxy terminated polyester of a dicarboxylic acid and a dihydric alcohol or phenol (a) with phosgene, or (b) with a bischloroformate of an an organic dihydroxy compound (especially a bis-phenol), or (c) first with phosgene to produce the bis-chloroformate of the polyester and then with an organic dihydroxy compound (especially a bis-phenol). Reaction is preferably effected in the presence of an organic or inorganic alkaline substance and an organic solvent (e.g. ethylene chloride or methylene chloride). In the manufacture of the polyester, the dicarboxylic acid may be succinic, adipic, azelaic, phthalic, terephthalic, maleic, fumaric or itaconic acid, the dihydric alcohol may be ethylene glycol, di- or tri-ethylene glycol, 1:2 or 1:3-propylene glycol, polymers of 1:3-propylene glycol, 1:4-butylene glycol, hexamethylene glycol, p-xylylene glycol, phthalylalcohol or 1:4- bis-(beta-hydroxyethyl)-benzene; and the dihydric phenol may be resorcinol, catechol, 4:41-bis-hydroxydiphenyl or bis-phenol A. In examples, copolymers are made by reacting (1) a polyester of terephthalic acid and hexamethylene glycol with the bis-chloroformate of bis-phenol A alone or in admixture with free bis-phenol A; (3) a polyester of ethylene glycol and maleic anhydride with a mixture of the bis-chloroformate of bis-phenol A and free bis-phenol A; (4) a polyester of terephthalic acid and hexamethylene glycol with phosgene; (5) a polyester of maleic anhydride, phthalic anhydride and diethylene glycol with the bischloroformate of bis-phenol A. The unsaturated polymers of Examples 3 and 5 may be homopolymerized or copolymerized with styrene by heating in the presence of peroxide catalysts (e.g. benzoyl peroxide or acetone peroxide). The polymers are useful in the manufacture of films, fibres, laminates, metal coatings, electrical insulation materials, potting compositions and mouldings. Reference has been directed by the Comptroller to Specification 870,095.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69805557A | 1957-11-22 | 1957-11-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB912203A true GB912203A (en) | 1962-12-05 |
Family
ID=24803741
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35033/61A Expired GB909613A (en) | 1957-11-22 | 1958-11-12 | Polycarbonate resins |
| GB3503261A Expired GB906790A (en) | 1957-11-22 | 1958-11-12 | Polycarbonates derived from diepoxy compounds |
| GB36350/58A Expired GB906012A (en) | 1957-11-22 | 1958-11-12 | Polymers containing carbonate and carbamate groups |
| GB35030/61A Expired GB912898A (en) | 1957-11-22 | 1958-11-12 | Unsaturated polycarbonate esters |
| GB35031/61A Expired GB912203A (en) | 1957-11-22 | 1958-11-12 | Mixed polycarbonate-polycarboxylic acid esters |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35033/61A Expired GB909613A (en) | 1957-11-22 | 1958-11-12 | Polycarbonate resins |
| GB3503261A Expired GB906790A (en) | 1957-11-22 | 1958-11-12 | Polycarbonates derived from diepoxy compounds |
| GB36350/58A Expired GB906012A (en) | 1957-11-22 | 1958-11-12 | Polymers containing carbonate and carbamate groups |
| GB35030/61A Expired GB912898A (en) | 1957-11-22 | 1958-11-12 | Unsaturated polycarbonate esters |
Country Status (4)
| Country | Link |
|---|---|
| CH (2) | CH396413A (en) |
| DE (3) | DE1420309A1 (en) |
| GB (5) | GB909613A (en) |
| NL (1) | NL129040C (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2435508C2 (en) * | 1974-07-24 | 1985-08-22 | Bayer Ag, 5090 Leverkusen | Flame-retardant polycarbonate molding compounds |
| DE2636783C2 (en) * | 1976-08-16 | 1982-10-21 | Bayer Ag, 5090 Leverkusen | Process for the production of high molecular weight, segmented, thermoplastically processable polyester-polycarbonates |
| US4476294A (en) * | 1983-12-16 | 1984-10-09 | General Electric Company | Copolyester-carbonate resins |
| US4728716A (en) * | 1985-11-12 | 1988-03-01 | General Electric Company | Polycarbonate exhibiting improved impact properties containing divalent residue of polymerized alkadiene monomer |
| CN115003723B (en) * | 2020-01-07 | 2023-12-05 | 诠达化学股份有限公司 | Thermoplastic polyurethane with high tensile strength, preparation formula and manufacturing method thereof |
-
1958
- 1958-11-12 GB GB35033/61A patent/GB909613A/en not_active Expired
- 1958-11-12 GB GB3503261A patent/GB906790A/en not_active Expired
- 1958-11-12 GB GB36350/58A patent/GB906012A/en not_active Expired
- 1958-11-12 GB GB35030/61A patent/GB912898A/en not_active Expired
- 1958-11-12 GB GB35031/61A patent/GB912203A/en not_active Expired
- 1958-11-19 DE DE19581420309 patent/DE1420309A1/en active Pending
- 1958-11-19 DE DE19581420278 patent/DE1420278A1/en active Pending
- 1958-11-19 DE DE19581520483 patent/DE1520483A1/en active Pending
- 1958-11-21 CH CH3765A patent/CH396413A/en unknown
- 1958-11-21 CH CH6644358A patent/CH398083A/en unknown
-
1964
- 1964-08-20 NL NL6409652A patent/NL129040C/en active
Also Published As
| Publication number | Publication date |
|---|---|
| CH398083A (en) | 1965-08-31 |
| NL129040C (en) | 1970-01-15 |
| GB909613A (en) | 1962-10-31 |
| GB912898A (en) | 1962-12-12 |
| CH396413A (en) | 1965-07-31 |
| DE1420309A1 (en) | 1969-02-20 |
| DE1420278A1 (en) | 1968-11-14 |
| NL6409652A (en) | 1964-10-12 |
| GB906012A (en) | 1962-09-19 |
| DE1520483A1 (en) | 1970-02-19 |
| GB906790A (en) | 1962-09-26 |
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