CH616431A5 - Process for the preparation of novel unsaturated phosphorus-containing carboxylic acid derivatives - Google Patents
Process for the preparation of novel unsaturated phosphorus-containing carboxylic acid derivatives Download PDFInfo
- Publication number
- CH616431A5 CH616431A5 CH1340675A CH1340675A CH616431A5 CH 616431 A5 CH616431 A5 CH 616431A5 CH 1340675 A CH1340675 A CH 1340675A CH 1340675 A CH1340675 A CH 1340675A CH 616431 A5 CH616431 A5 CH 616431A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- mol
- acid derivatives
- methyl
- carboxylic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 5
- 150000003017 phosphorus Chemical class 0.000 title description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 229910052698 phosphorus Inorganic materials 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- -1 methacrylic acid halide Chemical class 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000012442 inert solvent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 229940086542 triethylamine Drugs 0.000 description 6
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 5
- ZLVVDNKTHWEIOG-UHFFFAOYSA-N chloro(dimethyl)phosphane Chemical compound CP(C)Cl ZLVVDNKTHWEIOG-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 229950000688 phenothiazine Drugs 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- CDPKWOKGVUHZFR-UHFFFAOYSA-N dichloro(methyl)phosphane Chemical compound CP(Cl)Cl CDPKWOKGVUHZFR-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- UDQBLBPJVKUWET-UHFFFAOYSA-N 2-[methyl(2-methylpropoxy)phosphoryl]ethanol Chemical compound CC(C)COP(C)(=O)CCO UDQBLBPJVKUWET-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical group COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- WGSKFQLZKMECCJ-UHFFFAOYSA-N 2-hydroxyethyl(methyl)phosphinic acid Chemical compound CP(O)(=O)CCO WGSKFQLZKMECCJ-UHFFFAOYSA-N 0.000 description 1
- AQUWGZZBBPLEGC-UHFFFAOYSA-N 2-hydroxypropyl(methyl)phosphinic acid Chemical compound CC(O)CP(C)(O)=O AQUWGZZBBPLEGC-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- MLWHWVPMTLJDQS-UHFFFAOYSA-N CCOP(=O)CO Chemical compound CCOP(=O)CO MLWHWVPMTLJDQS-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- VHXAIGOQDLPGFR-UHFFFAOYSA-N OCCP(O)=S Chemical compound OCCP(O)=S VHXAIGOQDLPGFR-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- SLVYMKIHXNKKTE-UHFFFAOYSA-N [methyl(2-methylpropoxy)phosphoryl]methanol Chemical compound CC(C)COP(C)(=O)CO SLVYMKIHXNKKTE-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 1
- 229950007538 pecazine Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- 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
- C08F30/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F30/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3211—Esters of acyclic saturated acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2449466A DE2449466C2 (de) | 1974-10-19 | 1974-10-19 | Neue ungesättigte phosphorhaltige Carbonsäurederivate und Verfahren zu deren Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH616431A5 true CH616431A5 (en) | 1980-03-31 |
Family
ID=5928547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1340675A CH616431A5 (en) | 1974-10-19 | 1975-10-15 | Process for the preparation of novel unsaturated phosphorus-containing carboxylic acid derivatives |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5626676B2 (tr) |
| AT (1) | AT334398B (tr) |
| BE (1) | BE834672A (tr) |
| CA (1) | CA1053690A (tr) |
| CH (1) | CH616431A5 (tr) |
| DE (1) | DE2449466C2 (tr) |
| DK (1) | DK467675A (tr) |
| ES (1) | ES441741A1 (tr) |
| FR (1) | FR2288097A1 (tr) |
| GB (1) | GB1472699A (tr) |
| IE (1) | IE41812B1 (tr) |
| IT (1) | IT1043463B (tr) |
| LU (1) | LU73602A1 (tr) |
| NL (1) | NL7512062A (tr) |
| SE (1) | SE7511677L (tr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2841941A1 (de) * | 1978-09-27 | 1980-04-17 | Hoechst Ag | Organische phosphor-verbindungen mit 3-hydroxyalkylphosphinsaeureestergruppen |
| DE2918161A1 (de) * | 1979-05-05 | 1980-11-13 | Bayer Ag | Phosphonomaleinsaeureester sowie verfahren zu deren herstellung |
| DE102006012878A1 (de) * | 2006-03-21 | 2007-09-27 | Clariant International Limited | Phosphorhaltige Mischungen, ein Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE102006012881A1 (de) * | 2006-03-21 | 2007-09-27 | Clariant International Limited | Phosphorhaltige Mischungen, ein Verfahren zu ihrer Herstellung und ihre Verwendung |
| JP2008222677A (ja) * | 2007-03-15 | 2008-09-25 | Chisso Corp | 難燃剤、それを用いた重合体組成物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES396221A1 (es) * | 1970-10-27 | 1974-04-16 | Hoechst Ag | Procedimiento para la preparacion de derivados de acido carboxilico que contienen fosforo. |
-
1974
- 1974-10-19 DE DE2449466A patent/DE2449466C2/de not_active Expired
-
1975
- 1975-10-13 ES ES441741A patent/ES441741A1/es not_active Expired
- 1975-10-14 NL NL7512062A patent/NL7512062A/xx not_active Application Discontinuation
- 1975-10-15 CH CH1340675A patent/CH616431A5/de not_active IP Right Cessation
- 1975-10-17 GB GB4271675A patent/GB1472699A/en not_active Expired
- 1975-10-17 SE SE7511677A patent/SE7511677L/xx unknown
- 1975-10-17 IE IE2261/75A patent/IE41812B1/en unknown
- 1975-10-17 IT IT28410/75A patent/IT1043463B/it active
- 1975-10-17 AT AT791175A patent/AT334398B/de not_active IP Right Cessation
- 1975-10-17 DK DK467675A patent/DK467675A/da unknown
- 1975-10-17 LU LU73602A patent/LU73602A1/xx unknown
- 1975-10-17 FR FR7531811A patent/FR2288097A1/fr active Granted
- 1975-10-17 CA CA239,930A patent/CA1053690A/en not_active Expired
- 1975-10-17 JP JP12448775A patent/JPS5626676B2/ja not_active Expired
- 1975-10-20 BE BE161076A patent/BE834672A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT1043463B (it) | 1980-02-20 |
| IE41812L (en) | 1976-04-19 |
| DK467675A (da) | 1976-04-20 |
| FR2288097A1 (fr) | 1976-05-14 |
| ES441741A1 (es) | 1977-03-16 |
| LU73602A1 (tr) | 1976-08-19 |
| DE2449466A1 (de) | 1976-04-29 |
| JPS5626676B2 (tr) | 1981-06-19 |
| FR2288097B1 (tr) | 1979-01-05 |
| CA1053690A (en) | 1979-05-01 |
| JPS5180823A (tr) | 1976-07-15 |
| AT334398B (de) | 1976-01-10 |
| NL7512062A (nl) | 1976-04-21 |
| GB1472699A (en) | 1977-05-04 |
| SE7511677L (sv) | 1976-04-20 |
| BE834672A (fr) | 1976-04-20 |
| ATA791175A (de) | 1976-05-15 |
| DE2449466C2 (de) | 1982-07-15 |
| IE41812B1 (en) | 1980-03-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |