JP5374364B2 - 1,2,3,4−テトラクロロヘキサフルオロブタンの製造方法 - Google Patents
1,2,3,4−テトラクロロヘキサフルオロブタンの製造方法 Download PDFInfo
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- JP5374364B2 JP5374364B2 JP2009511794A JP2009511794A JP5374364B2 JP 5374364 B2 JP5374364 B2 JP 5374364B2 JP 2009511794 A JP2009511794 A JP 2009511794A JP 2009511794 A JP2009511794 A JP 2009511794A JP 5374364 B2 JP5374364 B2 JP 5374364B2
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- gas
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- fluorine
- tetrachlorohexafluorobutane
- producing
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- IRHYACQPDDXBCB-UHFFFAOYSA-N 1,2,3,4-tetrachloro-1,1,2,3,4,4-hexafluorobutane Chemical compound FC(F)(Cl)C(F)(Cl)C(F)(Cl)C(F)(F)Cl IRHYACQPDDXBCB-UHFFFAOYSA-N 0.000 title claims description 28
- 238000000034 method Methods 0.000 title description 16
- 239000007789 gas Substances 0.000 claims description 104
- 229910052731 fluorine Inorganic materials 0.000 claims description 96
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 94
- 239000011737 fluorine Substances 0.000 claims description 94
- 238000006243 chemical reaction Methods 0.000 claims description 57
- IXZVKECRTHXEEW-UHFFFAOYSA-N 1,2,3,4-tetrachlorobutane Chemical compound ClCC(Cl)C(Cl)CCl IXZVKECRTHXEEW-UHFFFAOYSA-N 0.000 claims description 45
- 238000004519 manufacturing process Methods 0.000 claims description 29
- 239000007788 liquid Substances 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 19
- XVEASTGLHPVZNA-UHFFFAOYSA-N 3,4-dichlorobut-1-ene Chemical compound ClCC(Cl)C=C XVEASTGLHPVZNA-UHFFFAOYSA-N 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 11
- 238000005660 chlorination reaction Methods 0.000 claims description 8
- 239000011261 inert gas Substances 0.000 claims description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 6
- KHFGPBNEILANTD-UHFFFAOYSA-N 1,1,1,2-tetrachloro-2,3,3,4,4,4-hexafluorobutane Chemical compound FC(F)(F)C(F)(F)C(F)(Cl)C(Cl)(Cl)Cl KHFGPBNEILANTD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 3
- 238000010790 dilution Methods 0.000 claims description 3
- 239000012895 dilution Substances 0.000 claims description 3
- 239000001307 helium Substances 0.000 claims description 3
- 229910052734 helium Inorganic materials 0.000 claims description 3
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052754 neon Inorganic materials 0.000 claims description 3
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 description 42
- 150000001875 compounds Chemical class 0.000 description 30
- 150000008282 halocarbons Chemical class 0.000 description 25
- 239000007810 chemical reaction solvent Substances 0.000 description 23
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 22
- 239000007791 liquid phase Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000007795 chemical reaction product Substances 0.000 description 10
- 238000003682 fluorination reaction Methods 0.000 description 10
- 238000000926 separation method Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 8
- 229920001084 poly(chloroprene) Polymers 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000005530 etching Methods 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 238000010926 purge Methods 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 239000004809 Teflon Substances 0.000 description 4
- 229920006362 Teflon® Polymers 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LGPPATCNSOSOQH-UHFFFAOYSA-N 1,1,2,3,4,4-hexafluorobuta-1,3-diene Chemical compound FC(F)=C(F)C(F)=C(F)F LGPPATCNSOSOQH-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000007809 chemical reaction catalyst Substances 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 150000001721 carbon Chemical class 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- FQDIANVAWVHZIR-OWOJBTEDSA-N trans-1,4-Dichlorobutene Chemical compound ClC\C=C\CCl FQDIANVAWVHZIR-OWOJBTEDSA-N 0.000 description 2
- BSRRYOGYBQJAFP-UHFFFAOYSA-N 1,1,1,2,2,3-hexafluorobutane Chemical compound CC(F)C(F)(F)C(F)(F)F BSRRYOGYBQJAFP-UHFFFAOYSA-N 0.000 description 1
- HGRZLIGHKHRTRE-UHFFFAOYSA-N 1,2,3,4-tetrabromobutane Chemical compound BrCC(Br)C(Br)CBr HGRZLIGHKHRTRE-UHFFFAOYSA-N 0.000 description 1
- XXRJJDKZTNVRFH-UHFFFAOYSA-N 1,2,3,4-tetraiodobutane Chemical compound ICC(I)C(I)CI XXRJJDKZTNVRFH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- -1 and for example Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical class FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 1
- 239000010702 perfluoropolyether Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(1)特開2006-342059号公報(特許文献1)には、CClX1X2−CClX3−CClX4−CClX5X6(Xは水素原子またはフッ素原子)で表されるハロゲン化化合物を、
液相中でフッ素ガスと接触させることにより1,2,3,4−テトラクロロヘキサフルオロブタンを製造する方法が記載されている。
工業的に生産されている1,3−ブタジエンの塩素化反応により主として3,4−ジクロロブテン−1および1,4−ジクロロブテン−2を生成させ、1,4−ジクロロブテン−2を異性化反応により3,4−ジクロロブテン−1として、蒸留分離により3,4−ジクロロブテン−1を得た。
この1,2,3,4−テトラクロロブタン中の異性体の割合は以下の通りであった。
<原料例2>
<原料例1>で得られた1,2,3,4−テトラクロロブタンを冷却(−20℃)し、メソ体を析出させて分離し、ガスクロマトグラフィーで分析を行った。結果を以下に示す。
この析出したメソ体を分離した後の1,2,3,4−テトラクロロブタン中の異性体の割合は以下の通りであった。
<原料例3>
<原料例2>で冷却し析出、分離し回収したメソ体を溶媒で再結晶させた。この成分についてガスクロマトグラフィーで分析を行った。結果を以下に示す。
この1,2,3,4−テトラクロロブタン中の異性体の割合は以下の通りであった。
[実施例1]
内容積200mlのSUS304製(テフロン(登録商標)ライニング)反応器に上記の原料例1で得られた1,2,3,4−テトラクロロブタン(dl体/メソ体=46/54)を30g(0.153mol)仕込み、窒素ガスを1.0MPaで導入して漏れテストを行った後、窒素ガスをパ−ジしながら反応器内のイナ−ト分を置換後、攪拌しながら反応器温度を15℃に保った。
結果から明らかなように、無溶媒かつ無触媒で収率よく目的物である1,2,3,4−テトラクロロヘキサフルオロブタンを得ることができる。
内容積200mlのSUS304製(テフロン(登録商標)ライニング)反応器に上記原料例2で得られた1,2,3,4−テトラクロロブタン(dl体/メソ体=91/9)を40g(0.204mol)仕込み、窒素ガスを1.0MPaで導入して漏れテストを行った後、窒素ガスをパ−ジしながら反応器内のイナ−ト分を置換後、攪拌しながら反応器温度を10℃に保った。
[実施例3]
内容積200mlのSUS304製(テフロン(登録商標)ライニング)反応器に上記の原料例3で得られた1,2,3,4−テトラクロロブタン(dl体/メソ体=3/97)を30g(0.153mol)仕込み、窒素ガスを1.5MPaで導入して漏れテストを行った後、窒素ガスをパ−ジしながら反応器内のイナ−ト分を置換後、攪拌しながら反応器温度を15℃に保った。
結果から明らかなように、室温で固体であるメソ体を用いても無溶媒で1,2,3,4−テトラクロロヘキサフルオロブタンを得ることができる。
Claims (8)
Priority Applications (1)
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JP2009511794A JP5374364B2 (ja) | 2007-04-20 | 2008-04-14 | 1,2,3,4−テトラクロロヘキサフルオロブタンの製造方法 |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007111750 | 2007-04-20 | ||
JP2007111750 | 2007-04-20 | ||
JP2009511794A JP5374364B2 (ja) | 2007-04-20 | 2008-04-14 | 1,2,3,4−テトラクロロヘキサフルオロブタンの製造方法 |
PCT/JP2008/057282 WO2008133086A1 (ja) | 2007-04-20 | 2008-04-14 | 含フッ素化合物の製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPWO2008133086A1 JPWO2008133086A1 (ja) | 2010-07-22 |
JP5374364B2 true JP5374364B2 (ja) | 2013-12-25 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2009511794A Active JP5374364B2 (ja) | 2007-04-20 | 2008-04-14 | 1,2,3,4−テトラクロロヘキサフルオロブタンの製造方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US8030528B2 (ja) |
JP (1) | JP5374364B2 (ja) |
KR (1) | KR101132492B1 (ja) |
CN (1) | CN101663257B (ja) |
TW (1) | TWI410395B (ja) |
WO (1) | WO2008133086A1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101357455B1 (ko) | 2008-05-16 | 2014-02-03 | 쇼와 덴코 가부시키가이샤 | 1,2,3,4-테트라클로로헥사플루오로부탄의 제조 방법 및 정제 방법 |
CN111212823B (zh) * | 2017-11-30 | 2022-06-24 | 昭和电工株式会社 | 1,2,3,4-四氯丁烷的制造方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01305041A (ja) * | 1988-06-01 | 1989-12-08 | Sagami Chem Res Center | フルオロハロアルカンの製造方法 |
JP2002539096A (ja) * | 1999-03-10 | 2002-11-19 | アライドシグナル インコーポレイテッド | フッ素化された化合物を製造する方法 |
JP2006342059A (ja) * | 2003-09-02 | 2006-12-21 | Asahi Glass Co Ltd | クロロフルオロブタンの製造方法 |
-
2008
- 2008-04-14 KR KR1020097024072A patent/KR101132492B1/ko active IP Right Grant
- 2008-04-14 WO PCT/JP2008/057282 patent/WO2008133086A1/ja active Application Filing
- 2008-04-14 CN CN2008800128807A patent/CN101663257B/zh active Active
- 2008-04-14 JP JP2009511794A patent/JP5374364B2/ja active Active
- 2008-04-14 US US12/596,568 patent/US8030528B2/en active Active
- 2008-04-18 TW TW097114356A patent/TWI410395B/zh active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01305041A (ja) * | 1988-06-01 | 1989-12-08 | Sagami Chem Res Center | フルオロハロアルカンの製造方法 |
JP2002539096A (ja) * | 1999-03-10 | 2002-11-19 | アライドシグナル インコーポレイテッド | フッ素化された化合物を製造する方法 |
JP2006342059A (ja) * | 2003-09-02 | 2006-12-21 | Asahi Glass Co Ltd | クロロフルオロブタンの製造方法 |
Also Published As
Publication number | Publication date |
---|---|
US20100121118A1 (en) | 2010-05-13 |
JPWO2008133086A1 (ja) | 2010-07-22 |
WO2008133086A1 (ja) | 2008-11-06 |
TW200909388A (en) | 2009-03-01 |
KR20090130250A (ko) | 2009-12-21 |
TWI410395B (zh) | 2013-10-01 |
CN101663257B (zh) | 2013-02-13 |
CN101663257A (zh) | 2010-03-03 |
US8030528B2 (en) | 2011-10-04 |
KR101132492B1 (ko) | 2012-03-30 |
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Free format text: JAPANESE INTERMEDIATE CODE: R350 |