NO131833B - - Google Patents
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- Publication number
- NO131833B NO131833B NO3282/70A NO328270A NO131833B NO 131833 B NO131833 B NO 131833B NO 3282/70 A NO3282/70 A NO 3282/70A NO 328270 A NO328270 A NO 328270A NO 131833 B NO131833 B NO 131833B
- Authority
- NO
- Norway
- Prior art keywords
- formamidine
- methyl
- dimethyl
- phenyl
- chlorine
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 21
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 150000001409 amidines Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002585 base Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000005660 chlorination reaction Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- STUSTWKEFDQFFZ-UHFFFAOYSA-N Chlordimeform Chemical compound CN(C)C=NC1=CC=C(Cl)C=C1C STUSTWKEFDQFFZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- -1 arylamine compound Chemical class 0.000 description 4
- VTJDEAHIKIEJET-UHFFFAOYSA-N n,n-dimethyl-n'-(2-methylphenyl)methanimidamide Chemical compound CN(C)C=NC1=CC=CC=C1C VTJDEAHIKIEJET-UHFFFAOYSA-N 0.000 description 4
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 4
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical class NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-ortho-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KDMQFDJFKUMIBQ-UHFFFAOYSA-N N,N-dimethyl-N'-(2-methylphenyl)methanimidamide hydrochloride Chemical compound Cl.CN(C=NC1=C(C=CC=C1)C)C KDMQFDJFKUMIBQ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ZPTXBCJETBDOAT-UHFFFAOYSA-N n'-(4-chlorophenyl)-n,n-dimethylmethanimidamide Chemical compound CN(C)C=NC1=CC=C(Cl)C=C1 ZPTXBCJETBDOAT-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BPEXTIMJLDWDTL-UHFFFAOYSA-N 2`-Methylacetanilide Chemical compound CC(=O)NC1=CC=CC=C1C BPEXTIMJLDWDTL-UHFFFAOYSA-N 0.000 description 1
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenylpropanol Natural products OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 241000326710 Argiope lobata Species 0.000 description 1
- BHIRITVVGWMZDM-UHFFFAOYSA-N Cl(=O)(=O)(=O)O.CN(C=NC1=C(C=CC=C1)C)C Chemical compound Cl(=O)(=O)(=O)O.CN(C=NC1=C(C=CC=C1)C)C BHIRITVVGWMZDM-UHFFFAOYSA-N 0.000 description 1
- BJSQROKDLFWALK-UHFFFAOYSA-N Cl.CC1=C(C=CC(=C1)Cl)C(=N)N Chemical compound Cl.CC1=C(C=CC(=C1)Cl)C(=N)N BJSQROKDLFWALK-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GUGRBFQNXVKOGR-UHFFFAOYSA-N butyl hypochlorite Chemical group CCCCOCl GUGRBFQNXVKOGR-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- SVZLJDOWISLDHE-UHFFFAOYSA-N n'-(4-chlorophenyl)methanimidamide Chemical compound ClC1=CC=C(NC=N)C=C1 SVZLJDOWISLDHE-UHFFFAOYSA-N 0.000 description 1
- SRPCLECGIYMIMN-UHFFFAOYSA-N n,n-dimethyl-n'-phenylmethanimidamide Chemical compound CN(C)C=NC1=CC=CC=C1 SRPCLECGIYMIMN-UHFFFAOYSA-N 0.000 description 1
- WMHHXYOPEQARIN-UHFFFAOYSA-N n-(4-chloro-2-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(Cl)C=C1C WMHHXYOPEQARIN-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- YOSXAXYCARLZTR-UHFFFAOYSA-N prop-2-enoyl isocyanate Chemical compound C=CC(=O)N=C=O YOSXAXYCARLZTR-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/12—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to hydrogen atoms
-
- E—FIXED CONSTRUCTIONS
- E02—HYDRAULIC ENGINEERING; FOUNDATIONS; SOIL SHIFTING
- E02D—FOUNDATIONS; EXCAVATIONS; EMBANKMENTS; UNDERGROUND OR UNDERWATER STRUCTURES
- E02D1/00—Investigation of foundation soil in situ
- E02D1/02—Investigation of foundation soil in situ before construction work
- E02D1/04—Sampling of soil
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- General Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Mining & Mineral Resources (AREA)
- Paleontology (AREA)
- Civil Engineering (AREA)
- Analytical Chemistry (AREA)
- Structural Engineering (AREA)
- Agronomy & Crop Science (AREA)
- Soil Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1944789A DE1944789C3 (de) | 1969-08-30 | 1969-08-30 | Verfahren zur Herstellung von 4-Chlorderivaten der Phenylformamidine und deren Salzen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO131833B true NO131833B (xx) | 1975-05-05 |
| NO131833C NO131833C (xx) | 1975-08-13 |
Family
ID=5744560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3282/70A NO131833C (xx) | 1969-08-30 | 1970-08-28 |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS541690B1 (xx) |
| AT (1) | AT301518B (xx) |
| BE (1) | BE755447A (xx) |
| BG (1) | BG21021A3 (xx) |
| CH (1) | CH547778A (xx) |
| CS (1) | CS162723B2 (xx) |
| DE (1) | DE1944789C3 (xx) |
| DK (1) | DK124476B (xx) |
| ES (1) | ES381345A1 (xx) |
| FI (1) | FI51474C (xx) |
| FR (1) | FR2059367A5 (xx) |
| IE (1) | IE34490B1 (xx) |
| IL (1) | IL35183A (xx) |
| LU (1) | LU61598A1 (xx) |
| NL (1) | NL169176C (xx) |
| NO (1) | NO131833C (xx) |
| OA (1) | OA03472A (xx) |
| PH (1) | PH9534A (xx) |
| PL (1) | PL81033B1 (xx) |
| RO (1) | RO58403A (xx) |
| SE (1) | SE372523B (xx) |
| TR (1) | TR20236A (xx) |
| YU (1) | YU35240B (xx) |
| ZA (1) | ZA705805B (xx) |
-
0
- BE BE755447D patent/BE755447A/xx not_active IP Right Cessation
-
1969
- 1969-08-30 DE DE1944789A patent/DE1944789C3/de not_active Expired
-
1970
- 1970-05-27 RO RO63457A patent/RO58403A/ro unknown
- 1970-06-09 CH CH865170A patent/CH547778A/xx not_active IP Right Cessation
- 1970-06-09 FI FI701632A patent/FI51474C/fi active
- 1970-06-15 CS CS4171*BA patent/CS162723B2/cs unknown
- 1970-06-27 BG BG015037A patent/BG21021A3/xx unknown
- 1970-07-01 ES ES381345A patent/ES381345A1/es not_active Expired
- 1970-07-03 YU YU1695/70A patent/YU35240B/xx unknown
- 1970-08-06 DK DK406270AA patent/DK124476B/da unknown
- 1970-08-12 PH PH11735*UA patent/PH9534A/en unknown
- 1970-08-20 OA OA54012A patent/OA03472A/xx unknown
- 1970-08-24 ZA ZA705805A patent/ZA705805B/xx unknown
- 1970-08-25 IE IE1111/70A patent/IE34490B1/xx unknown
- 1970-08-28 FR FR7031470A patent/FR2059367A5/fr not_active Expired
- 1970-08-28 SE SE7011763A patent/SE372523B/xx unknown
- 1970-08-28 IL IL35183A patent/IL35183A/xx unknown
- 1970-08-28 AT AT784670A patent/AT301518B/de not_active IP Right Cessation
- 1970-08-28 LU LU61598D patent/LU61598A1/xx unknown
- 1970-08-28 NO NO3282/70A patent/NO131833C/no unknown
- 1970-08-28 NL NLAANVRAGE7012814,A patent/NL169176C/xx not_active IP Right Cessation
- 1970-08-29 PL PL1970142931A patent/PL81033B1/pl unknown
- 1970-08-31 JP JP7624070A patent/JPS541690B1/ja active Pending
-
1977
- 1977-06-02 TR TR20236A patent/TR20236A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO131833C (xx) | 1975-08-13 |
| DE1944789B2 (de) | 1978-03-09 |
| AT301518B (de) | 1972-09-11 |
| YU35240B (en) | 1980-10-31 |
| JPS541690B1 (xx) | 1979-01-27 |
| BE755447A (fr) | 1971-03-01 |
| PH9534A (en) | 1976-01-09 |
| SU363243A3 (xx) | 1972-12-30 |
| NL7012814A (xx) | 1971-03-02 |
| ZA705805B (en) | 1971-04-28 |
| NL169176C (nl) | 1982-06-16 |
| CH547778A (de) | 1974-04-11 |
| DE1944789C3 (de) | 1978-11-09 |
| PL81033B1 (xx) | 1975-08-30 |
| IL35183A0 (en) | 1971-02-25 |
| IE34490L (en) | 1971-02-28 |
| CS162723B2 (xx) | 1975-07-15 |
| DK124476B (da) | 1972-10-23 |
| NL169176B (nl) | 1982-01-18 |
| OA03472A (fr) | 1971-03-30 |
| TR20236A (tr) | 1980-11-01 |
| RO58403A (xx) | 1975-09-15 |
| IL35183A (en) | 1974-07-31 |
| FI51474B (xx) | 1976-09-30 |
| FR2059367A5 (en) | 1971-05-28 |
| LU61598A1 (xx) | 1970-11-10 |
| FI51474C (fi) | 1977-01-10 |
| ES381345A1 (es) | 1972-12-01 |
| SE372523B (xx) | 1974-12-23 |
| BG21021A3 (bg) | 1976-01-20 |
| DE1944789A1 (de) | 1971-03-04 |
| IE34490B1 (en) | 1975-05-28 |
| YU169570A (en) | 1980-04-30 |
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