DE2238920C3 - Verfahren zur Herstellung von Polyaminen - Google Patents
Verfahren zur Herstellung von PolyaminenInfo
- Publication number
- DE2238920C3 DE2238920C3 DE2238920A DE2238920A DE2238920C3 DE 2238920 C3 DE2238920 C3 DE 2238920C3 DE 2238920 A DE2238920 A DE 2238920A DE 2238920 A DE2238920 A DE 2238920A DE 2238920 C3 DE2238920 C3 DE 2238920C3
- Authority
- DE
- Germany
- Prior art keywords
- formaldehyde
- mixture
- condensation
- acidic
- aromatic amine
- 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
- 238000000034 method Methods 0.000 title claims description 32
- 229920000768 polyamine Polymers 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 77
- 150000004982 aromatic amines Chemical class 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 32
- 239000003054 catalyst Substances 0.000 claims description 26
- 230000002378 acidificating effect Effects 0.000 claims description 25
- 238000009833 condensation Methods 0.000 claims description 25
- 230000005494 condensation Effects 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 15
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 230000002209 hydrophobic effect Effects 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000003377 acid catalyst Substances 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- UTNMPUFESIRPQP-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC=C1N UTNMPUFESIRPQP-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 4
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- -1 amine ammonium salts Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- WKBALTUBRZPIPZ-UHFFFAOYSA-N 2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N WKBALTUBRZPIPZ-UHFFFAOYSA-N 0.000 description 1
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- RHZOPAIIGWFYGN-UHFFFAOYSA-N aniline;hydrate;hydrochloride Chemical compound O.Cl.NC1=CC=CC=C1 RHZOPAIIGWFYGN-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical class C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/45—Monoamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2238920A DE2238920C3 (de) | 1972-08-08 | 1972-08-08 | Verfahren zur Herstellung von Polyaminen |
| CA177,440A CA1004234A (en) | 1972-08-04 | 1973-07-26 | Process for the production of polyamines |
| US05/383,921 US3996283A (en) | 1972-08-04 | 1973-07-30 | Process for the production of polyamines |
| NLAANVRAGE7310656,A NL180416C (nl) | 1972-08-04 | 1973-08-01 | Werkwijze voor de bereiding van uit enkele kernen bestaande, aromatische primaire polyaminen. |
| BR5886/73A BR7305886D0 (pt) | 1972-08-08 | 1973-08-02 | Processo para a preparacao de poliaminas |
| GB3696573A GB1404680A (en) | 1972-08-08 | 1973-08-03 | Process for the production of polyamines |
| JP8691273A JPS5720937B2 (enrdf_load_stackoverflow) | 1972-08-08 | 1973-08-03 | |
| BE134238A BE803217A (fr) | 1972-08-08 | 1973-08-03 | Procede de preparation de polyamines |
| FR7328533A FR2195620B1 (enrdf_load_stackoverflow) | 1972-08-08 | 1973-08-03 | |
| PL1973164530A PL86402B1 (enrdf_load_stackoverflow) | 1972-08-08 | 1973-08-06 | |
| AT687773A AT329876B (de) | 1972-08-08 | 1973-08-06 | Verfahren zur herstellung von mehrkernigen aromatischen polyaminen |
| IT51867/73A IT990159B (it) | 1972-08-08 | 1973-08-06 | Procedimento ed apparecchiatura per produrre poliammine |
| CH1136473A CH584182A5 (enrdf_load_stackoverflow) | 1972-08-08 | 1973-08-06 | |
| DD172731A DD109009A5 (enrdf_load_stackoverflow) | 1972-08-08 | 1973-08-06 | |
| ES417633A ES417633A1 (es) | 1972-08-08 | 1973-08-07 | Procedimiento para la obtencion de poliaminas aromaticas multinucleares. |
| AU58977/73A AU473924B2 (en) | 1972-08-08 | 1973-08-07 | Process forthe production of polyamines |
| SU1957740A SU497765A3 (ru) | 1972-08-08 | 1973-08-07 | Способ получени полиаминов |
| SE7310821A SE403283B (sv) | 1972-08-08 | 1973-08-07 | Sett att framstella flerkerniga, aromatiska aminer genom kondensation av aromatiska aminer med formaldehyd i nervaro av vatten och sura katalysatorer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2238920A DE2238920C3 (de) | 1972-08-08 | 1972-08-08 | Verfahren zur Herstellung von Polyaminen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2238920A1 DE2238920A1 (de) | 1974-03-07 |
| DE2238920B2 DE2238920B2 (de) | 1979-05-03 |
| DE2238920C3 true DE2238920C3 (de) | 1984-09-27 |
Family
ID=5852969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2238920A Expired DE2238920C3 (de) | 1972-08-04 | 1972-08-08 | Verfahren zur Herstellung von Polyaminen |
Country Status (15)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2648982C2 (de) * | 1975-11-11 | 1985-07-11 | Efim Zürich Biller | Verfahren zur Herstellung von Methylenbrücken aufweisenden Polyarylaminen |
| DE2557500A1 (de) * | 1975-12-19 | 1977-06-30 | Bayer Ag | Verfahren zur herstellung von polyaminen |
| DE2557501A1 (de) * | 1975-12-19 | 1977-06-30 | Bayer Ag | Verfahren zur herstellung von polyaminen |
| US4201722A (en) * | 1976-06-04 | 1980-05-06 | The Upjohn Company | Process for separating 4,4'-diaminodiphenylmethane |
| DE2748968A1 (de) * | 1976-11-06 | 1978-05-11 | Elprochine Ag | Verfahren zur herstellung von methylenbruecken aufweisenden polyarylaminen |
| US4294987A (en) * | 1979-12-31 | 1981-10-13 | The Upjohn Company | Process for preparing methylene dianilines |
| BRPI0619159B1 (pt) * | 2005-12-08 | 2016-04-12 | Huntsman Int Llc | processo para a preparação de diamino difenil metano e poli-(diamino difenil metano), e, processo para a preparação de metileno difenileno diisocianato e poli-(metileno difenileno diisocianato) |
| EP2039676A1 (en) * | 2007-09-19 | 2009-03-25 | Huntsman International Llc | Process for the production of di-and polyamines of the diphenylmethane series |
| DE102008012037A1 (de) | 2008-03-01 | 2009-09-03 | Bayer Materialscience Ag | Verfahren zur Herstellung von Methylen-diphenyl-diisocyanaten |
| DE102008015123A1 (de) * | 2008-03-20 | 2009-09-24 | Bayer Materialscience Ag | Verfahren zur Herstellung von Di- und Polyaminen der Diphenylmethanreihe |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1026322B (de) * | 1956-02-14 | 1958-03-20 | Basf Ag | Verfahren zur Herstellung von 4, 4'-Bis-(dialkylamino)-diphenylmethanen |
| NL293671A (enrdf_load_stackoverflow) * | 1962-06-06 | |||
| DE1179945B (de) * | 1962-12-11 | 1964-10-22 | Basf Ag | Verfahren zur Herstellung von 4, 4'-Diaminodiphenylmethanen |
| FR1359549A (fr) * | 1963-06-06 | 1964-04-24 | Geigy Ag J R | Nouvelles méthylène-anilines à activité nématocide, leur préparation et leur application pour le traitement des plantes |
| FR1429551A (fr) * | 1964-02-28 | 1966-02-25 | Kaiser Aluminium Chem Corp | Procédé de production de polyamines primaires |
| US3358025A (en) * | 1964-09-14 | 1967-12-12 | Upjohn Co | Process of recovering 4, 4'-methylenedi |
| JPS4516691Y1 (enrdf_load_stackoverflow) * | 1966-09-29 | 1970-07-10 | ||
| ES356415A1 (es) * | 1967-08-07 | 1970-01-01 | Upjohn Co | Procedimiento para la preparacion de di (aminofenil) meta- no. |
| DE1800073A1 (de) * | 1968-10-01 | 1970-05-21 | Nii Chimikatov Dlja Polimernyc | Verfahren zur Herstellung von 3,3'-Dichlor-4,4'-diaminodiphenylmethan |
| BE757094R (fr) * | 1969-10-06 | 1971-04-06 | Upjohn Co | Procede de preparation de di(aminophenyl)methane |
| HUH2984A (en) * | 1970-03-02 | 1970-03-02 | Magyar Tudomanyos Akademia | Process for producing diamino-diphenylmethane |
-
1972
- 1972-08-08 DE DE2238920A patent/DE2238920C3/de not_active Expired
-
1973
- 1973-08-02 BR BR5886/73A patent/BR7305886D0/pt unknown
- 1973-08-03 GB GB3696573A patent/GB1404680A/en not_active Expired
- 1973-08-03 JP JP8691273A patent/JPS5720937B2/ja not_active Expired
- 1973-08-03 BE BE134238A patent/BE803217A/xx not_active IP Right Cessation
- 1973-08-03 FR FR7328533A patent/FR2195620B1/fr not_active Expired
- 1973-08-06 PL PL1973164530A patent/PL86402B1/pl unknown
- 1973-08-06 AT AT687773A patent/AT329876B/de not_active IP Right Cessation
- 1973-08-06 IT IT51867/73A patent/IT990159B/it active
- 1973-08-06 DD DD172731A patent/DD109009A5/xx unknown
- 1973-08-06 CH CH1136473A patent/CH584182A5/xx not_active IP Right Cessation
- 1973-08-07 SE SE7310821A patent/SE403283B/xx unknown
- 1973-08-07 SU SU1957740A patent/SU497765A3/ru active
- 1973-08-07 AU AU58977/73A patent/AU473924B2/en not_active Expired
- 1973-08-07 ES ES417633A patent/ES417633A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5720937B2 (enrdf_load_stackoverflow) | 1982-05-04 |
| JPS4953687A (enrdf_load_stackoverflow) | 1974-05-24 |
| ATA687773A (de) | 1975-08-15 |
| DE2238920B2 (de) | 1979-05-03 |
| SU497765A3 (ru) | 1975-12-30 |
| FR2195620B1 (enrdf_load_stackoverflow) | 1976-11-12 |
| PL86402B1 (enrdf_load_stackoverflow) | 1976-05-31 |
| DD109009A5 (enrdf_load_stackoverflow) | 1974-10-12 |
| DE2238920A1 (de) | 1974-03-07 |
| BR7305886D0 (pt) | 1974-05-16 |
| AT329876B (de) | 1976-06-10 |
| GB1404680A (en) | 1975-09-03 |
| BE803217A (fr) | 1974-02-04 |
| IT990159B (it) | 1975-06-20 |
| ES417633A1 (es) | 1976-02-16 |
| AU5897773A (en) | 1975-02-13 |
| FR2195620A1 (enrdf_load_stackoverflow) | 1974-03-08 |
| SE403283B (sv) | 1978-08-07 |
| CH584182A5 (enrdf_load_stackoverflow) | 1977-01-31 |
| AU473924B2 (en) | 1976-07-08 |
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