JP2837190B2 - メタクリルオキシ基またはアクリルオキシ基を有するオルガノシランの安定化法 - Google Patents
メタクリルオキシ基またはアクリルオキシ基を有するオルガノシランの安定化法Info
- Publication number
- JP2837190B2 JP2837190B2 JP1248255A JP24825589A JP2837190B2 JP 2837190 B2 JP2837190 B2 JP 2837190B2 JP 1248255 A JP1248255 A JP 1248255A JP 24825589 A JP24825589 A JP 24825589A JP 2837190 B2 JP2837190 B2 JP 2837190B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- phenylenediamine
- organosilane
- distillation
- methacryloxy
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 10
- -1 methacryloxy group Chemical group 0.000 title claims description 17
- 150000001282 organosilanes Chemical class 0.000 title claims description 4
- 230000006641 stabilisation Effects 0.000 title description 3
- 238000011105 stabilization Methods 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 claims description 5
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims 2
- 229910000077 silane Inorganic materials 0.000 abstract description 13
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000001624 naphthyl group Chemical group 0.000 abstract description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 abstract 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical class NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000003019 stabilising effect Effects 0.000 abstract 1
- 238000004821 distillation Methods 0.000 description 16
- 239000003381 stabilizer Substances 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 9
- 150000002989 phenols Chemical class 0.000 description 8
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
- 241000482268 Zea mays subsp. mays Species 0.000 description 7
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- ZRMMVODKVLXCBB-UHFFFAOYSA-N 1-n-cyclohexyl-4-n-phenylbenzene-1,4-diamine Chemical group C1CCCCC1NC(C=C1)=CC=C1NC1=CC=CC=C1 ZRMMVODKVLXCBB-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- VETPHHXZEJAYOB-UHFFFAOYSA-N 1-n,4-n-dinaphthalen-2-ylbenzene-1,4-diamine Chemical compound C1=CC=CC2=CC(NC=3C=CC(NC=4C=C5C=CC=CC5=CC=4)=CC=3)=CC=C21 VETPHHXZEJAYOB-UHFFFAOYSA-N 0.000 description 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 1
- NZLCQKJFPRPJMG-UHFFFAOYSA-N 2,6-ditert-butyl-4-ethylphenol;2,6-ditert-butyl-4-methylphenol Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1.CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NZLCQKJFPRPJMG-UHFFFAOYSA-N 0.000 description 1
- OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical group C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/20—Purification, separation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3832621A DE3832621C1 (enExample) | 1988-09-26 | 1988-09-26 | |
| DE3832621.3 | 1988-09-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02129191A JPH02129191A (ja) | 1990-05-17 |
| JP2837190B2 true JP2837190B2 (ja) | 1998-12-14 |
Family
ID=6363716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1248255A Expired - Fee Related JP2837190B2 (ja) | 1988-09-26 | 1989-09-26 | メタクリルオキシ基またはアクリルオキシ基を有するオルガノシランの安定化法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4927948A (enExample) |
| EP (1) | EP0361325B1 (enExample) |
| JP (1) | JP2837190B2 (enExample) |
| AT (1) | ATE116323T1 (enExample) |
| DD (1) | DD284881A5 (enExample) |
| DE (2) | DE3832621C1 (enExample) |
| ES (1) | ES2066821T3 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4021869A1 (de) * | 1990-07-09 | 1992-01-16 | Huels Chemische Werke Ag | Verfahren zur verhinderung von verfaerbungen in vinylacetoxysilanen |
| JPH04117390A (ja) * | 1990-09-05 | 1992-04-17 | Tonen Corp | γ―メタクリロキシプロピルシラン化合物の製造方法 |
| JPH04117389A (ja) * | 1990-09-05 | 1992-04-17 | Tonen Corp | γ―メタクリロキシプロピルシラン化合物の製造方法 |
| JP2552950B2 (ja) * | 1990-11-13 | 1996-11-13 | 信越化学工業株式会社 | アルコキシシランの製造方法 |
| US5103032A (en) * | 1991-06-27 | 1992-04-07 | Union Carbide Chemicals & Plastics Technology Corporation | Inhibited acryloxysilanes and methacryloxysilanes |
| JP2501052B2 (ja) * | 1991-09-04 | 1996-05-29 | 信越化学工業株式会社 | 有機けい素化合物の着色防止方法 |
| DE4430729C2 (de) * | 1994-08-30 | 2002-05-23 | Degussa | Acryloxypropylalkoxysilane, Verfahren zu deren Herstellung und deren Verwendung |
| DE4437667A1 (de) | 1994-10-21 | 1996-04-25 | Huels Chemische Werke Ag | Verfahren zur Herstellung von N,N'-disubstituierten p-Chinondiiminen, deren Verwendung und Methacryloxy- oder Acryloxy-Gruppen enthaltende Organosilane, Verfahren zu deren Stabilisierung und deren Herstellung |
| DE4437666A1 (de) | 1994-10-21 | 1996-04-25 | Huels Chemische Werke Ag | Verfahren zur Herstellung von N,N-disubstituierten p-Chinondiiminen und deren Verwendung |
| US5616712A (en) * | 1995-05-16 | 1997-04-01 | Allergan | Acetylenes disubstituted with a phenyl or heteroaryl group and a 2-thio-1,2,3,4-tetrahdroquinolinyl, 2-alkylthio-3,4-dihydroquinolinyl or 2-alkoxy-3,4-dihydroquinolinyl group having retinoid-like biological activity |
| US5824195A (en) * | 1995-07-10 | 1998-10-20 | Chisso Corporation | Process for distilling crude acrylic silane solution |
| DE10118489C1 (de) * | 2001-04-12 | 2002-07-25 | Wacker Chemie Gmbh | Verfahren zur Herstellung ungesättigter Organosiliciumverbindungen |
| US20030065177A1 (en) * | 2001-08-08 | 2003-04-03 | Crompton Corporation, A Corporation Of The State Of Delaware | High boiling inhibitors for distillable, polymerizable monomers |
| DE10258982B3 (de) * | 2002-12-16 | 2004-08-05 | Degussa Ag | Verfahren zur Herstellung von Acryloxy- oder Methacryloxygruppen enthaltenden Organosilanen höchster Reinheit |
| DE102005057459A1 (de) | 2005-12-01 | 2007-06-06 | Wacker Chemie Ag | Verfahren zur Herstellung ungesättigter Organosiliciumverbindungen |
| DE102008040475A1 (de) | 2008-07-16 | 2010-01-21 | Wacker Chemie Ag | Verfahren zur Verhinderung der Polymerisation von ungesättigten Organosiliciumverbindungen |
| DE102008042679A1 (de) | 2008-10-08 | 2010-04-15 | Wacker Chemie Ag | Verfahren zur Darstellung von (Meth-)Acrylsilanen |
| DE102013214830A1 (de) | 2013-07-30 | 2015-02-05 | Evonik Industries Ag | Verfahren, Vorrichtung und deren Verwendung zur Herstellung von Acryloxy- und Methacryloxypropyltrialkoxysilanen |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2389802A (en) * | 1945-11-27 | Stabilizing organo-siloxanes | ||
| CA736504A (en) * | 1966-06-14 | Dow Corning Corporation | Stabilization of acryloxy propyl-methoxy silanes | |
| US2389803A (en) * | 1945-11-27 | Stabilizing okgano-silosanss | ||
| US2517536A (en) * | 1946-06-28 | 1950-08-08 | Universal Oil Prod Co | Stabilization of organo-siloxanes |
| US2697114A (en) * | 1946-06-28 | 1954-12-14 | Universal Oil Prod Co | Stabilization of organo-siloxanes |
| BE787750A (fr) * | 1971-08-20 | 1973-02-19 | Union Carbide Corp | Procede pour inhiber la polymerisation d'acrylates et methacrylates pendant leur distillation |
| JPS5940158B2 (ja) * | 1975-12-15 | 1984-09-28 | 三菱マテリアル株式会社 | オルガノシランノセイゾウホウホウ |
| US4709067A (en) * | 1986-05-20 | 1987-11-24 | Union Carbide Corporation | Method for preparing methacryloxy and acryloxy containing organosilanes and organosilicones |
| JPS63188689A (ja) * | 1987-01-30 | 1988-08-04 | Toa Nenryo Kogyo Kk | γ−メタクリロキシプロピルシラン類の製造方法 |
| US4754046A (en) * | 1987-06-25 | 1988-06-28 | Dow Corning Corporation | Stabilized silyl ketene acetals |
| US4798889A (en) * | 1987-11-13 | 1989-01-17 | Dow Corning Corporation | Method for stabilizing unsaturated organosilicone compositions |
| US4780555A (en) * | 1988-01-04 | 1988-10-25 | Dow Corning Corporation | Method for preparing and stabilizing acryl-functional halosilanes |
-
1988
- 1988-09-26 DE DE3832621A patent/DE3832621C1/de not_active Expired
-
1989
- 1989-09-19 US US07/409,604 patent/US4927948A/en not_active Expired - Lifetime
- 1989-09-22 AT AT89117537T patent/ATE116323T1/de not_active IP Right Cessation
- 1989-09-22 EP EP89117537A patent/EP0361325B1/de not_active Expired - Lifetime
- 1989-09-22 ES ES89117537T patent/ES2066821T3/es not_active Expired - Lifetime
- 1989-09-22 DE DE58908830T patent/DE58908830D1/de not_active Expired - Fee Related
- 1989-09-25 DD DD89332939A patent/DD284881A5/de not_active IP Right Cessation
- 1989-09-26 JP JP1248255A patent/JP2837190B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0361325A3 (de) | 1991-01-09 |
| US4927948A (en) | 1990-05-22 |
| EP0361325A2 (de) | 1990-04-04 |
| ES2066821T3 (es) | 1995-03-16 |
| DE3832621C1 (enExample) | 1989-09-21 |
| DE58908830D1 (de) | 1995-02-09 |
| DD284881A5 (de) | 1990-11-28 |
| JPH02129191A (ja) | 1990-05-17 |
| ATE116323T1 (de) | 1995-01-15 |
| EP0361325B1 (de) | 1994-12-28 |
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