CN101052624A - 生产封端型异氰酸酯化合物的方法 - Google Patents
生产封端型异氰酸酯化合物的方法 Download PDFInfo
- Publication number
- CN101052624A CN101052624A CNA2005800374066A CN200580037406A CN101052624A CN 101052624 A CN101052624 A CN 101052624A CN A2005800374066 A CNA2005800374066 A CN A2005800374066A CN 200580037406 A CN200580037406 A CN 200580037406A CN 101052624 A CN101052624 A CN 101052624A
- Authority
- CN
- China
- Prior art keywords
- isocyanate compound
- compound
- blocked isocyanate
- iii
- ethylenically unsaturated
- 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
- -1 isocyanate compound Chemical class 0.000 title claims abstract description 264
- 239000012948 isocyanate Substances 0.000 title claims abstract description 192
- 238000000034 method Methods 0.000 title claims abstract description 107
- 230000008569 process Effects 0.000 title abstract description 32
- 238000004519 manufacturing process Methods 0.000 claims abstract description 43
- 238000006243 chemical reaction Methods 0.000 claims description 87
- 238000006116 polymerization reaction Methods 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000006185 dispersion Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001118 alkylidene group Chemical group 0.000 claims description 5
- 238000005304 joining Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 18
- 239000012442 inert solvent Substances 0.000 abstract description 14
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract description 11
- 239000006227 byproduct Substances 0.000 abstract description 7
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 238000010420 art technique Methods 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 239000012778 molding material Substances 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 70
- 239000000047 product Substances 0.000 description 34
- 238000010521 absorption reaction Methods 0.000 description 31
- 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 description 26
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 26
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- 239000012263 liquid product Substances 0.000 description 14
- 238000010992 reflux Methods 0.000 description 13
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 7
- 238000000465 moulding Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 235000014347 soups Nutrition 0.000 description 3
- JEHFRMABGJJCPF-UHFFFAOYSA-N 2-methylprop-2-enoyl isocyanate Chemical compound CC(=C)C(=O)N=C=O JEHFRMABGJJCPF-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003217 pyrazoles Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
- C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
- C07D231/32—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
Claims (16)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004316577 | 2004-10-29 | ||
JP316577/2004 | 2004-10-29 | ||
PCT/JP2005/020151 WO2006046758A1 (en) | 2004-10-29 | 2005-10-27 | Process for producing blocked isocyanate compound |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101052624A true CN101052624A (zh) | 2007-10-10 |
CN101052624B CN101052624B (zh) | 2010-05-12 |
Family
ID=38190917
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2005800374066A Active CN101052624B (zh) | 2004-10-29 | 2005-10-27 | 生产封端型异氰酸酯化合物的方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US7504518B2 (zh) |
EP (1) | EP1812402B1 (zh) |
JP (1) | JP4879557B2 (zh) |
KR (1) | KR100891790B1 (zh) |
CN (1) | CN101052624B (zh) |
TW (1) | TW200626529A (zh) |
WO (1) | WO2006046758A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102844297A (zh) * | 2010-04-14 | 2012-12-26 | 3M创新有限公司 | 制备异氰酸酯的方法 |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5685839B2 (ja) * | 2010-06-23 | 2015-03-18 | 日油株式会社 | 防曇塗料組成物 |
US9970246B2 (en) | 2012-04-09 | 2018-05-15 | M-I L.L.C. | Triggered heating of wellbore fluids by carbon nanomaterials |
KR101651030B1 (ko) | 2012-07-30 | 2016-08-24 | 쇼와 덴코 가부시키가이샤 | 블록 이소시아네이트 화합물의 제조 방법 |
JP5673885B1 (ja) * | 2013-08-02 | 2015-02-18 | ダイキン工業株式会社 | 不飽和基を有する新規化合物及びこの化合物を含む組成物 |
KR101808968B1 (ko) | 2013-08-02 | 2017-12-13 | 다이킨 고교 가부시키가이샤 | 중합성 관능기 및 가교성 관능기로 이루어지는 군에서 선택되는 적어도 1종의 기를 함유하는 불소 함유 중합체를 포함하는 조성물 및 도장물품 |
KR101957476B1 (ko) | 2017-03-24 | 2019-03-12 | 한국화학연구원 | 이중 경화가 가능한 저온가교형 블록이소시아네이트 및 이를 포함하는 조성물 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2612783C3 (de) * | 1976-03-25 | 1981-11-05 | Hoechst Ag, 6000 Frankfurt | Biurete, Verfahren zu ihrer Herstellung und deren Verwendung |
DE3046409A1 (de) | 1980-12-10 | 1982-07-15 | Bayer Ag, 5090 Leverkusen | Beschichtungsmittel und ein verfahren zur herstellung von ueberzuegen |
US5246557A (en) * | 1984-02-29 | 1993-09-21 | The Baxenden Chemical Co. | Blocked isocyanates |
JPH0749462B2 (ja) | 1989-06-14 | 1995-05-31 | 日本ポリウレタン工業株式会社 | ブロックイソシアネート化合物、並びにこれを含有する低温硬化性組成物、塗料組成物及び接着剤組成物 |
US5395721A (en) * | 1992-03-02 | 1995-03-07 | Fuji Photo Film Co., Ltd. | Electrophotographic material for color proofing |
JP3276440B2 (ja) | 1992-03-02 | 2002-04-22 | 富士写真フイルム株式会社 | 電子写真式色校正用原版 |
US5626996A (en) * | 1992-06-04 | 1997-05-06 | Fuji Photo Film Co., Ltd. | Electrophotographic material for color proofing |
FR2717178B1 (fr) * | 1994-03-14 | 1997-01-31 | Hoechst France | Résines acrylate-styrène réticulée par un polyisocyanate bloqué, préparation et applications comme peinture et/ou vernis. |
DE4416750A1 (de) | 1994-05-13 | 1995-11-16 | Bayer Ag | Mischblockierte Polyisocyanate |
DE4441418A1 (de) * | 1994-11-22 | 1996-05-23 | Bayer Ag | Verfahren zur Herstellung von 3,5-Dimethylpyrazol-blockierten Polyisocyanaten |
JP3781862B2 (ja) | 1997-05-19 | 2006-05-31 | 昭和電工株式会社 | 硬化性組成物 |
-
2005
- 2005-10-27 CN CN2005800374066A patent/CN101052624B/zh active Active
- 2005-10-27 WO PCT/JP2005/020151 patent/WO2006046758A1/en active Application Filing
- 2005-10-27 KR KR1020077011948A patent/KR100891790B1/ko active IP Right Grant
- 2005-10-27 EP EP05800038.1A patent/EP1812402B1/en active Active
- 2005-10-27 US US11/666,696 patent/US7504518B2/en not_active Expired - Fee Related
- 2005-10-28 TW TW094137933A patent/TW200626529A/zh unknown
- 2005-10-31 JP JP2005316071A patent/JP4879557B2/ja active Active
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102844297A (zh) * | 2010-04-14 | 2012-12-26 | 3M创新有限公司 | 制备异氰酸酯的方法 |
CN102844297B (zh) * | 2010-04-14 | 2014-12-10 | 3M创新有限公司 | 制备异氰酸酯的方法 |
Also Published As
Publication number | Publication date |
---|---|
WO2006046758A1 (en) | 2006-05-04 |
JP4879557B2 (ja) | 2012-02-22 |
US20070265454A1 (en) | 2007-11-15 |
EP1812402A1 (en) | 2007-08-01 |
TWI308562B (zh) | 2009-04-11 |
US7504518B2 (en) | 2009-03-17 |
EP1812402B1 (en) | 2013-07-17 |
KR20070073940A (ko) | 2007-07-10 |
JP2006151967A (ja) | 2006-06-15 |
TW200626529A (en) | 2006-08-01 |
CN101052624B (zh) | 2010-05-12 |
KR100891790B1 (ko) | 2009-04-07 |
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Correction item: Inventor Correct: Miyada Hideo|Murakami Jungmin|Ono Seungjun False: Miyada Hideo|Murakami Masami|Ono Seungjun Number: 19 Volume: 26 |
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CI03 | Correction of invention patent |
Correction item: Inventor Correct: Miyata Hideo|Murakami Jungmin|Ono Seungjun False: Miyata Hideo|Murakami Masami|Ono Seungjun Number: 19 Page: The title page Volume: 26 |
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Address after: Tokyo, Japan Patentee after: Lishennoco Co.,Ltd. Address before: Tokyo, Japan Patentee before: Showa electrical materials Co.,Ltd. |
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