DE2014469A1 - Neue Azoverbindungen, deren Herstellung und Verwendung - Google Patents
Neue Azoverbindungen, deren Herstellung und VerwendungInfo
- Publication number
- DE2014469A1 DE2014469A1 DE19702014469 DE2014469A DE2014469A1 DE 2014469 A1 DE2014469 A1 DE 2014469A1 DE 19702014469 DE19702014469 DE 19702014469 DE 2014469 A DE2014469 A DE 2014469A DE 2014469 A1 DE2014469 A1 DE 2014469A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- group
- hydrogen atom
- compounds
- formula
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- -1 heterocyclic radical Chemical class 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000000975 dye Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- 125000004442 acylamino group Chemical group 0.000 claims description 9
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229920002678 cellulose Polymers 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 4
- 125000001302 tertiary amino group Chemical group 0.000 claims description 4
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 238000004040 coloring Methods 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 235000021190 leftovers Nutrition 0.000 claims 1
- 238000009987 spinning Methods 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- FENJKTQEFUPECW-UHFFFAOYSA-N 3-anilinopropanenitrile Chemical compound N#CCCNC1=CC=CC=C1 FENJKTQEFUPECW-UHFFFAOYSA-N 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-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
- 239000003086 colorant Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- YAZSBRQTAHVVGE-UHFFFAOYSA-N 2-aminobenzenesulfonamide Chemical class NC1=CC=CC=C1S(N)(=O)=O YAZSBRQTAHVVGE-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000010902 straw Substances 0.000 description 2
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 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 group 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 1
- SXKGTORQDOFQDA-UHFFFAOYSA-N 2-amino-N-ethyl-4-methoxy-N-phenylbenzenesulfonamide Chemical compound C=1C=C(OC)C=C(N)C=1S(=O)(=O)N(CC)C1=CC=CC=C1 SXKGTORQDOFQDA-UHFFFAOYSA-N 0.000 description 1
- SRSKRCCFJHIKHI-UHFFFAOYSA-N 2-amino-n,n-dibutylbenzenesulfonamide Chemical compound CCCCN(CCCC)S(=O)(=O)C1=CC=CC=C1N SRSKRCCFJHIKHI-UHFFFAOYSA-N 0.000 description 1
- XRSRTHMYXNCEEB-UHFFFAOYSA-N 2-amino-n-butylbenzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC=CC=C1N XRSRTHMYXNCEEB-UHFFFAOYSA-N 0.000 description 1
- TUENGZHHNXAVMJ-UHFFFAOYSA-N 2-amino-n-cyclohexylbenzenesulfonamide Chemical compound NC1=CC=CC=C1S(=O)(=O)NC1CCCCC1 TUENGZHHNXAVMJ-UHFFFAOYSA-N 0.000 description 1
- AGSWRZMLPKYDNM-UHFFFAOYSA-N 2-amino-n-ethyl-5-nitro-n-phenylbenzenesulfonamide Chemical compound C=1C([N+]([O-])=O)=CC=C(N)C=1S(=O)(=O)N(CC)C1=CC=CC=C1 AGSWRZMLPKYDNM-UHFFFAOYSA-N 0.000 description 1
- HQAVWQUPULBREU-UHFFFAOYSA-N 2-amino-n-ethylbenzenesulfonamide Chemical compound CCNS(=O)(=O)C1=CC=CC=C1N HQAVWQUPULBREU-UHFFFAOYSA-N 0.000 description 1
- SSEZSHJJNNLTQI-UHFFFAOYSA-N 2-amino-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1N SSEZSHJJNNLTQI-UHFFFAOYSA-N 0.000 description 1
- PFMDLZQSUMZMHZ-UHFFFAOYSA-N 2-amino-n-propan-2-ylbenzenesulfonamide Chemical compound CC(C)NS(=O)(=O)C1=CC=CC=C1N PFMDLZQSUMZMHZ-UHFFFAOYSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- FZMXXXBUHOWPTC-UHFFFAOYSA-N 2-anilinoethyl acetate Chemical compound CC(=O)OCCNC1=CC=CC=C1 FZMXXXBUHOWPTC-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- ZAISDHPZTZIFQF-UHFFFAOYSA-N 2h-1,4-thiazine Chemical compound C1SC=CN=C1 ZAISDHPZTZIFQF-UHFFFAOYSA-N 0.000 description 1
- IXXLKTZOCSRXEM-UHFFFAOYSA-N 3-(n-methylanilino)propanenitrile Chemical compound N#CCCN(C)C1=CC=CC=C1 IXXLKTZOCSRXEM-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- VWOWEJYQHLKNFC-UHFFFAOYSA-N CC1=CC=CC(S(N(C)C2=CC=CC=C2)(=O)=O)=C1N Chemical compound CC1=CC=CC(S(N(C)C2=CC=CC=C2)(=O)=O)=C1N VWOWEJYQHLKNFC-UHFFFAOYSA-N 0.000 description 1
- 229920013660 Cellon Polymers 0.000 description 1
- 229920002160 Celluloid Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 206010039587 Scarlet Fever Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical group NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000000578 dry spinning Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- NDDVNVNAPACOLF-UHFFFAOYSA-N n-ethyl-n-(2-methoxyethyl)aniline Chemical compound COCCN(CC)C1=CC=CC=C1 NDDVNVNAPACOLF-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- XQVIOVDBTVZJER-UHFFFAOYSA-N propyl 3-anilinopropanoate Chemical compound CCCOC(=O)CCNC1=CC=CC=C1 XQVIOVDBTVZJER-UHFFFAOYSA-N 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000002166 wet spinning Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/06—Dyes
Landscapes
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH510569A CH515969A (de) | 1969-04-02 | 1969-04-02 | Verfahren zur Herstellung von Azofarbstoffen |
| CH1800569 | 1969-12-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2014469A1 true DE2014469A1 (de) | 1970-10-08 |
Family
ID=25696975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702014469 Pending DE2014469A1 (de) | 1969-04-02 | 1970-03-25 | Neue Azoverbindungen, deren Herstellung und Verwendung |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4928651B1 (enrdf_load_stackoverflow) |
| BE (1) | BE748288A (enrdf_load_stackoverflow) |
| CA (1) | CA925076A (enrdf_load_stackoverflow) |
| DE (1) | DE2014469A1 (enrdf_load_stackoverflow) |
| ES (1) | ES378114A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2049063B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1286906A (enrdf_load_stackoverflow) |
| NL (1) | NL7004631A (enrdf_load_stackoverflow) |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2251813A (en) * | 1939-05-23 | 1941-08-05 | American Cyanamid Co | Azo dye |
| US2261175A (en) * | 1939-07-01 | 1941-11-04 | Eastman Kodak Co | Azo compounds and material colored therewith |
| US2373700A (en) * | 1940-06-29 | 1945-04-17 | Eastman Kodak Co | Azo compounds and material colored therewith |
| US2347704A (en) * | 1942-01-08 | 1944-05-02 | Eastman Kodak Co | Azo compounds |
| US2373407A (en) * | 1943-06-26 | 1945-04-10 | Eastman Kodak Co | Azo compounds |
| CH427081A (de) * | 1956-07-18 | 1966-12-31 | Sandoz Ag | Verfahren zur Herstellung wasserunlöslicher Azofarbstoffe |
| FR73019E (fr) * | 1957-07-23 | 1960-09-22 | Sandoz Ag | Colorants mono-azoïques insolubles dans l'eau, leur procédé de préparation et leurs applications |
| CH349951A (de) * | 1959-03-05 | 1960-11-15 | Sandoz Ag | Haltbares Färbepräparat |
| GB993162A (en) * | 1962-04-17 | 1965-05-26 | Ici Ltd | New water-insoluble monoazo dyestuffs |
| NL130113C (enrdf_load_stackoverflow) * | 1964-08-26 |
-
1970
- 1970-02-16 CA CA074918A patent/CA925076A/en not_active Expired
- 1970-02-23 FR FR7006378A patent/FR2049063B1/fr not_active Expired
- 1970-03-04 GB GB1041770A patent/GB1286906A/en not_active Expired
- 1970-03-25 DE DE19702014469 patent/DE2014469A1/de active Pending
- 1970-03-30 JP JP2604270A patent/JPS4928651B1/ja active Pending
- 1970-04-01 NL NL7004631A patent/NL7004631A/xx unknown
- 1970-04-01 ES ES378114A patent/ES378114A1/es not_active Expired
- 1970-04-01 BE BE748288D patent/BE748288A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE748288A (fr) | 1970-10-01 |
| GB1286906A (en) | 1972-08-31 |
| FR2049063A1 (enrdf_load_stackoverflow) | 1971-03-26 |
| ES378114A1 (es) | 1973-01-01 |
| CA925076A (en) | 1973-04-24 |
| NL7004631A (enrdf_load_stackoverflow) | 1970-10-06 |
| FR2049063B1 (enrdf_load_stackoverflow) | 1973-05-25 |
| JPS4928651B1 (enrdf_load_stackoverflow) | 1974-07-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHN | Withdrawal |