DE2636865C3 - Aromatische N,N,N',N'-Tetraacetyldiaminverbindungen und Verfahren zu deren Herstellung - Google Patents
Aromatische N,N,N',N'-Tetraacetyldiaminverbindungen und Verfahren zu deren HerstellungInfo
- Publication number
- DE2636865C3 DE2636865C3 DE2636865A DE2636865A DE2636865C3 DE 2636865 C3 DE2636865 C3 DE 2636865C3 DE 2636865 A DE2636865 A DE 2636865A DE 2636865 A DE2636865 A DE 2636865A DE 2636865 C3 DE2636865 C3 DE 2636865C3
- Authority
- DE
- Germany
- Prior art keywords
- tetraacetyl
- yarn
- aromatic
- compounds
- flame
- 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
- 125000003118 aryl group Chemical group 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 8
- -1 diamine compounds Chemical class 0.000 title claims description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 31
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 150000004984 aromatic diamines Chemical class 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000001118 alkylidene group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- OJONPYPYSRNGQR-UHFFFAOYSA-N n-acetyl-n-[2,6-dibromo-4-[3,5-dibromo-4-(diacetylamino)phenyl]phenyl]acetamide Chemical compound C1=C(Br)C(N(C(C)=O)C(=O)C)=C(Br)C=C1C1=CC(Br)=C(N(C(C)=O)C(C)=O)C(Br)=C1 OJONPYPYSRNGQR-UHFFFAOYSA-N 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 229910052727 yttrium Inorganic materials 0.000 claims 1
- 239000004952 Polyamide Substances 0.000 description 27
- 229920002647 polyamide Polymers 0.000 description 27
- 239000012264 purified product Substances 0.000 description 21
- 238000010521 absorption reaction Methods 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 12
- 229920002292 Nylon 6 Polymers 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000012043 crude product Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- 239000000835 fiber Substances 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 239000003063 flame retardant Substances 0.000 description 5
- 238000009987 spinning Methods 0.000 description 5
- 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 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- NAVMNUFNDGIZTG-UHFFFAOYSA-N 2,4,6-tribromobenzene-1,3-diamine Chemical compound NC1=C(Br)C=C(Br)C(N)=C1Br NAVMNUFNDGIZTG-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- BFXPLVFGMOQHPK-UHFFFAOYSA-N n-acetyl-n-[2,4,6-tribromo-3-(diacetylamino)phenyl]acetamide Chemical compound CC(=O)N(C(C)=O)C1=C(Br)C=C(Br)C(N(C(C)=O)C(C)=O)=C1Br BFXPLVFGMOQHPK-UHFFFAOYSA-N 0.000 description 3
- XTKYSLZALZKOFZ-UHFFFAOYSA-N n-acetyl-n-[2,4,6-trichloro-3-(diacetylamino)phenyl]acetamide Chemical compound CC(=O)N(C(C)=O)C1=C(Cl)C=C(Cl)C(N(C(C)=O)C(C)=O)=C1Cl XTKYSLZALZKOFZ-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- XIYZGUDKXQSHCJ-UHFFFAOYSA-N 2,4,6-trichlorobenzene-1,3-diamine Chemical compound NC1=C(Cl)C=C(Cl)C(N)=C1Cl XIYZGUDKXQSHCJ-UHFFFAOYSA-N 0.000 description 2
- KIMCSKCETOAMBU-UHFFFAOYSA-N 4-[2-(4-amino-3,5-dibromophenyl)propan-2-yl]-2,6-dibromoaniline Chemical compound C=1C(Br)=C(N)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(N)C(Br)=C1 KIMCSKCETOAMBU-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000009940 knitting Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- MJFBGMMDLNKGNC-UHFFFAOYSA-N 2,5-dibromobenzene-1,4-diamine Chemical compound NC1=CC(Br)=C(N)C=C1Br MJFBGMMDLNKGNC-UHFFFAOYSA-N 0.000 description 1
- QAYVHDDEMLNVMO-UHFFFAOYSA-N 2,5-dichlorobenzene-1,4-diamine Chemical compound NC1=CC(Cl)=C(N)C=C1Cl QAYVHDDEMLNVMO-UHFFFAOYSA-N 0.000 description 1
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 1
- LHECBTWFKAHFAS-UHFFFAOYSA-N 4-(4-aminophenyl)-6,6-dichlorocyclohexa-1,3-dien-1-amine Chemical group C1C(Cl)(Cl)C(N)=CC=C1C1=CC=C(N)C=C1 LHECBTWFKAHFAS-UHFFFAOYSA-N 0.000 description 1
- WPBDGAXSVITBCN-UHFFFAOYSA-N 4-[2-(4-amino-3,5-dibromophenyl)ethyl]-2,6-dibromoaniline Chemical group C1=C(Br)C(N)=C(Br)C=C1CCC1=CC(Br)=C(N)C(Br)=C1 WPBDGAXSVITBCN-UHFFFAOYSA-N 0.000 description 1
- BJVXGTDQYUXCRB-UHFFFAOYSA-N 4-[2-(4-amino-3,5-dichlorophenyl)propan-2-yl]-2,6-dichloroaniline Chemical compound C=1C(Cl)=C(N)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(N)C(Cl)=C1 BJVXGTDQYUXCRB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- CMQSCKMAHGAPEE-UHFFFAOYSA-N bis(4-amino-3,5-dichlorophenyl)methanone Chemical compound C1=C(Cl)C(N)=C(Cl)C=C1C(=O)C1=CC(Cl)=C(N)C(Cl)=C1 CMQSCKMAHGAPEE-UHFFFAOYSA-N 0.000 description 1
- BKKDOKZWVFDQMM-UHFFFAOYSA-N bis(4-amino-3-chlorophenyl)methanone Chemical compound C1=C(Cl)C(N)=CC=C1C(=O)C1=CC=C(N)C(Cl)=C1 BKKDOKZWVFDQMM-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- VOFNHCVTIMDROI-UHFFFAOYSA-N n-acetyl-n-[2,5-dibromo-4-(diacetylamino)phenyl]acetamide Chemical compound CC(=O)N(C(C)=O)C1=CC(Br)=C(N(C(C)=O)C(C)=O)C=C1Br VOFNHCVTIMDROI-UHFFFAOYSA-N 0.000 description 1
- SJPBZTWPPJKLBP-UHFFFAOYSA-N n-acetyl-n-[2,5-dichloro-4-(diacetylamino)phenyl]acetamide Chemical compound CC(=O)N(C(C)=O)C1=CC(Cl)=C(N(C(C)=O)C(C)=O)C=C1Cl SJPBZTWPPJKLBP-UHFFFAOYSA-N 0.000 description 1
- ISLKLIKFGUKRQY-UHFFFAOYSA-N n-acetyl-n-[2,6-dibromo-4-[2-[3,5-dibromo-4-(diacetylamino)phenyl]propan-2-yl]phenyl]acetamide Chemical compound C1=C(Br)C(N(C(C)=O)C(=O)C)=C(Br)C=C1C(C)(C)C1=CC(Br)=C(N(C(C)=O)C(C)=O)C(Br)=C1 ISLKLIKFGUKRQY-UHFFFAOYSA-N 0.000 description 1
- XXDWPADMPRYLKP-UHFFFAOYSA-N n-acetyl-n-[2,6-dibromo-4-[3,5-dibromo-4-(diacetylamino)benzoyl]phenyl]acetamide Chemical compound C1=C(Br)C(N(C(C)=O)C(=O)C)=C(Br)C=C1C(=O)C1=CC(Br)=C(N(C(C)=O)C(C)=O)C(Br)=C1 XXDWPADMPRYLKP-UHFFFAOYSA-N 0.000 description 1
- MTMWWLJBMBBVND-UHFFFAOYSA-N n-acetyl-n-[2,6-dichloro-4-[2-[3,5-dichloro-4-(diacetylamino)phenyl]propan-2-yl]phenyl]acetamide Chemical compound C1=C(Cl)C(N(C(C)=O)C(=O)C)=C(Cl)C=C1C(C)(C)C1=CC(Cl)=C(N(C(C)=O)C(C)=O)C(Cl)=C1 MTMWWLJBMBBVND-UHFFFAOYSA-N 0.000 description 1
- WRUWWRNRXFKDOX-UHFFFAOYSA-N n-acetyl-n-[2,6-dichloro-4-[3,5-dichloro-4-(diacetylamino)benzoyl]phenyl]acetamide Chemical compound C1=C(Cl)C(N(C(C)=O)C(=O)C)=C(Cl)C=C1C(=O)C1=CC(Cl)=C(N(C(C)=O)C(C)=O)C(Cl)=C1 WRUWWRNRXFKDOX-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Artificial Filaments (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polyamides (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10046875A JPS5225117A (en) | 1975-08-18 | 1975-08-18 | Prepapation of flame retardant polyamide |
| JP12394775A JPS5248633A (en) | 1975-10-14 | 1975-10-14 | Process for preparation of n,n,n',n'-tetraacylated and nuclear halogen ated aromatic diamines |
| JP4693076A JPS52131535A (en) | 1976-04-24 | 1976-04-24 | Novel aromatic diamine compound and fire-retarding polyamide resinous composition containing same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2636865A1 DE2636865A1 (de) | 1977-03-03 |
| DE2636865B2 DE2636865B2 (de) | 1978-11-16 |
| DE2636865C3 true DE2636865C3 (de) | 1982-03-18 |
Family
ID=27292807
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2636865A Expired DE2636865C3 (de) | 1975-08-18 | 1976-08-17 | Aromatische N,N,N',N'-Tetraacetyldiaminverbindungen und Verfahren zu deren Herstellung |
| DE2660075A Expired DE2660075C2 (de) | 1975-08-18 | 1976-08-17 | Flammbestandige Polyamidmassen und -fasern |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2660075A Expired DE2660075C2 (de) | 1975-08-18 | 1976-08-17 | Flammbestandige Polyamidmassen und -fasern |
Country Status (7)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4359538A (en) * | 1979-03-20 | 1982-11-16 | Labofina, S.A. | Fire-retardant polystyrenic compositions |
| US4725455A (en) * | 1984-06-01 | 1988-02-16 | Colgate-Palmolive Company | Process for manufacturing particulate built nonionic synthetic organic detergent composition comprising polyacetal carboxylate and polyphosphate builders |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2560939A (en) * | 1951-07-17 | - methylenebis | ||
| US2028715A (en) * | 1931-04-27 | 1936-01-21 | Halowax Corp | Fire resistant composition |
| US2443255A (en) * | 1942-10-02 | 1948-06-15 | Du Pont | Derivatives of 2-aminc-diphenylsulfone |
| US2986491A (en) * | 1959-01-02 | 1961-05-30 | Velsicol Chemical Corp | Production of pesticidal compounds |
| NL265877A (US08088918-20120103-C00476.png) * | 1960-06-27 | |||
| US3189647A (en) * | 1961-11-29 | 1965-06-15 | Universal Oil Prod Co | N-acyl-diaminodiphenyl ethers |
| NL6604975A (US08088918-20120103-C00476.png) * | 1965-04-22 | 1966-10-24 | ||
| US3557211A (en) * | 1967-10-25 | 1971-01-19 | Tenneco Chem | Substituted n,n'-bis(acetyl)-o-phenylene diamines |
| US3539629A (en) * | 1968-03-13 | 1970-11-10 | Fmc Corp | Process for producing tetraacetyl derivatives of diamines |
| US3663620A (en) * | 1969-12-09 | 1972-05-16 | Millmaster Onyx Corp | N-(halogenated biphenyl)-diethylene triamines |
| DE2046795B2 (de) * | 1970-09-23 | 1975-05-07 | Chemische Fabrik Kalk Gmbh, 5000 Koeln | Selbstverlöschende Formmassen auf der Basis von Acrylnitril-Butadien-Styrol-Polymerisaten |
| DE2052822C3 (de) * | 1970-10-28 | 1979-04-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von N,N,N',N'-Tetraacetyläthylendiamin |
| US3846469A (en) * | 1972-06-12 | 1974-11-05 | Dow Chemical Co | Isopropylidene bis(2,6-dihalo-p-phenylene) bis(poly-halophenyl) carbonates |
| US3886212A (en) * | 1973-02-19 | 1975-05-27 | Wacker Chemie Gmbh | Process for preparing N,N,N{40 ,N{40 -tetraacetyl compounds |
-
1976
- 1976-08-12 US US05/713,651 patent/US4144225A/en not_active Expired - Lifetime
- 1976-08-16 GB GB33942/76A patent/GB1517864A/en not_active Expired
- 1976-08-17 CA CA259,271A patent/CA1109488A/en not_active Expired
- 1976-08-17 DE DE2636865A patent/DE2636865C3/de not_active Expired
- 1976-08-17 DE DE2660075A patent/DE2660075C2/de not_active Expired
- 1976-08-18 FR FR7625126A patent/FR2321483A1/fr active Granted
- 1976-08-18 NL NLAANVRAGE7609160,A patent/NL169603C/xx not_active IP Right Cessation
- 1976-08-18 IT IT26340/76A patent/IT1065150B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2321483A1 (fr) | 1977-03-18 |
| AU1671676A (en) | 1977-09-22 |
| NL169603C (nl) | 1982-08-02 |
| US4144225A (en) | 1979-03-13 |
| DE2660075C2 (de) | 1980-06-19 |
| NL169603B (nl) | 1982-03-01 |
| NL7609160A (nl) | 1977-02-22 |
| DE2636865B2 (de) | 1978-11-16 |
| CA1109488A (en) | 1981-09-22 |
| IT1065150B (it) | 1985-02-25 |
| DE2636865A1 (de) | 1977-03-03 |
| GB1517864A (en) | 1978-07-12 |
| FR2321483B1 (US08088918-20120103-C00476.png) | 1978-10-06 |
| DE2660075B1 (de) | 1979-09-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OI | Miscellaneous see part 1 | ||
| OI | Miscellaneous see part 1 | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |