DE2128002B2 - - Google Patents
Info
- Publication number
- DE2128002B2 DE2128002B2 DE19712128002 DE2128002A DE2128002B2 DE 2128002 B2 DE2128002 B2 DE 2128002B2 DE 19712128002 DE19712128002 DE 19712128002 DE 2128002 A DE2128002 A DE 2128002A DE 2128002 B2 DE2128002 B2 DE 2128002B2
- Authority
- DE
- Germany
- Prior art keywords
- weight
- parts
- copolymer
- vinylpyrrolidone
- clear
- 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.)
- Granted
Links
- 229920001577 copolymer Polymers 0.000 claims description 54
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 23
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims description 21
- 239000000835 fiber Substances 0.000 claims description 17
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 11
- 229920002959 polymer blend Polymers 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 41
- 239000000243 solution Substances 0.000 description 28
- 229920000642 polymer Polymers 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 210000003934 vacuole Anatomy 0.000 description 20
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 18
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 9
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000009987 spinning Methods 0.000 description 5
- FOSCIVJDUKVDMS-UHFFFAOYSA-N C1=CC=CC=C1.C(C(=C)C)(=O)NC1=CC=CC=C1 Chemical compound C1=CC=CC=C1.C(C(=C)C)(=O)NC1=CC=CC=C1 FOSCIVJDUKVDMS-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- HLKZFSVWBQSKKH-UHFFFAOYSA-N but-3-enoic acid;1-ethenylpyrrolidin-2-one Chemical compound OC(=O)CC=C.C=CN1CCCC1=O HLKZFSVWBQSKKH-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- FAYOHXXNNWBUMY-UHFFFAOYSA-N 1-(2-aminophenyl)-2-methylprop-2-en-1-one;benzene Chemical compound C1=CC=CC=C1.CC(=C)C(=O)C1=CC=CC=C1N FAYOHXXNNWBUMY-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic alcohols Chemical class 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 1
- PSCBFLUKTNBZFX-UHFFFAOYSA-N 1-(2-aminophenyl)prop-2-en-1-one benzene Chemical compound C1=CC=CC=C1.NC1=CC=CC=C1C(=O)C=C PSCBFLUKTNBZFX-UHFFFAOYSA-N 0.000 description 1
- XEEYSDHEOQHCDA-UHFFFAOYSA-N 2-methylprop-2-ene-1-sulfonic acid Chemical compound CC(=C)CS(O)(=O)=O XEEYSDHEOQHCDA-UHFFFAOYSA-N 0.000 description 1
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- XPKXOXQVRUWHEA-UHFFFAOYSA-N acetic acid but-1-en-2-ol Chemical compound C(C)(=O)O.C(C)(=O)O.C=C(CC)O XPKXOXQVRUWHEA-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002788 crimping Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- QUXJSCAOGVQXNK-UHFFFAOYSA-N formaldehyde;sodium;sulfanediol Chemical compound [Na].O=C.OSO QUXJSCAOGVQXNK-UHFFFAOYSA-N 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical class OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000002166 wet spinning Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/18—Homopolymers or copolymers of nitriles
- C08L33/20—Homopolymers or copolymers of acrylonitrile
-
- 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
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/44—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds
- D01F6/54—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds of polymers of unsaturated nitriles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
- C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
- C08L39/06—Homopolymers or copolymers of N-vinyl-pyrrolidones
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Artificial Filaments (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19712128002 DE2128002C3 (de) | 1971-06-05 | 1971-06-05 | Glanzstabile Filme, Fäden und Fasern aus Copolymerisat-Mischungen auf der Basis von Acrylnitril-Copolymerisaten |
GB2559272A GB1386993A (en) | 1971-06-05 | 1972-06-01 | Films and fibres of acrylonitrile polymer compositions |
DD16335972A DD97661A5 (en, 2012) | 1971-06-05 | 1972-06-01 | |
BE784328A BE784328A (fr) | 1971-06-05 | 1972-06-02 | Pellicules, filaments et fibres a brillant permanent |
AT477672A AT315512B (de) | 1971-06-05 | 1972-06-02 | Glanzstabile Filme, Fäden und Fasern aus Copolymerisat-Mischungen auf der Basis von Acrylnitril-Copolymerisaten sowie Verfahren und Spinnlösung zur Herstellung derselben |
CA143,701A CA990884A (en) | 1971-06-05 | 1972-06-02 | Gloss-stable films, filaments and fibres of copolymer mixtures based on acrylonitrile copolymers |
IT2522672A IT961212B (it) | 1971-06-05 | 1972-06-03 | Pellicole filamenti e fibre a lu centezza stabile di miscele di copolimeri a base di copolimeri acrilonitrilici |
ES403494A ES403494A1 (es) | 1971-06-05 | 1972-06-03 | Procedimiento para la obtencion de peliculas, hilos y fi- bras de brillo estable. |
JP5520972A JPS5517782B1 (en, 2012) | 1971-06-05 | 1972-06-05 | |
FR7220160A FR2141188A5 (en, 2012) | 1971-06-05 | 1972-06-05 | |
NL7207608A NL7207608A (en, 2012) | 1971-06-05 | 1972-06-05 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19712128002 DE2128002C3 (de) | 1971-06-05 | 1971-06-05 | Glanzstabile Filme, Fäden und Fasern aus Copolymerisat-Mischungen auf der Basis von Acrylnitril-Copolymerisaten |
Publications (3)
Publication Number | Publication Date |
---|---|
DE2128002A1 DE2128002A1 (de) | 1973-01-04 |
DE2128002B2 true DE2128002B2 (en, 2012) | 1978-03-30 |
DE2128002C3 DE2128002C3 (de) | 1978-11-30 |
Family
ID=5809948
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19712128002 Expired DE2128002C3 (de) | 1971-06-05 | 1971-06-05 | Glanzstabile Filme, Fäden und Fasern aus Copolymerisat-Mischungen auf der Basis von Acrylnitril-Copolymerisaten |
Country Status (11)
Country | Link |
---|---|
JP (1) | JPS5517782B1 (en, 2012) |
AT (1) | AT315512B (en, 2012) |
BE (1) | BE784328A (en, 2012) |
CA (1) | CA990884A (en, 2012) |
DD (1) | DD97661A5 (en, 2012) |
DE (1) | DE2128002C3 (en, 2012) |
ES (1) | ES403494A1 (en, 2012) |
FR (1) | FR2141188A5 (en, 2012) |
GB (1) | GB1386993A (en, 2012) |
IT (1) | IT961212B (en, 2012) |
NL (1) | NL7207608A (en, 2012) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1033934A (en) * | 1973-07-09 | 1978-07-04 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Wet-spinning polyacrylonitrile into organic aqueous solution |
DE2558384C3 (de) * | 1975-12-23 | 1984-11-08 | Bayer Ag, 5090 Leverkusen | Glanzstabile Modacrylfasern und -fäden und Verfahren zu ihrer Herstellung |
GB2130566B (en) * | 1982-09-24 | 1986-07-09 | Chevron Res | Recovering metals from spent hydroprocessing catalysts |
JP5941820B2 (ja) * | 2012-10-23 | 2016-06-29 | 東京応化工業株式会社 | レジスト組成物、レジストパターン形成方法及び高分子化合物 |
-
1971
- 1971-06-05 DE DE19712128002 patent/DE2128002C3/de not_active Expired
-
1972
- 1972-06-01 DD DD16335972A patent/DD97661A5/xx unknown
- 1972-06-01 GB GB2559272A patent/GB1386993A/en not_active Expired
- 1972-06-02 BE BE784328A patent/BE784328A/xx unknown
- 1972-06-02 AT AT477672A patent/AT315512B/de not_active IP Right Cessation
- 1972-06-02 CA CA143,701A patent/CA990884A/en not_active Expired
- 1972-06-03 ES ES403494A patent/ES403494A1/es not_active Expired
- 1972-06-03 IT IT2522672A patent/IT961212B/it active
- 1972-06-05 NL NL7207608A patent/NL7207608A/xx not_active Application Discontinuation
- 1972-06-05 FR FR7220160A patent/FR2141188A5/fr not_active Expired
- 1972-06-05 JP JP5520972A patent/JPS5517782B1/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
JPS5517782B1 (en, 2012) | 1980-05-14 |
FR2141188A5 (en, 2012) | 1973-01-19 |
IT961212B (it) | 1973-12-10 |
CA990884A (en) | 1976-06-08 |
DE2128002C3 (de) | 1978-11-30 |
DD97661A5 (en, 2012) | 1973-05-12 |
GB1386993A (en) | 1975-03-12 |
DE2128002A1 (de) | 1973-01-04 |
AT315512B (de) | 1974-05-27 |
NL7207608A (en, 2012) | 1972-12-07 |
ES403494A1 (es) | 1975-05-01 |
BE784328A (fr) | 1972-12-04 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
C3 | Grant after two publication steps (3rd publication) | ||
8339 | Ceased/non-payment of the annual fee |