JPS6222756A - 新規なペルフルオロ（ｎ−ビニル環状アミン）の製造方法 - Google Patents
新規なペルフルオロ（ｎ−ビニル環状アミン）の製造方法Info
- Publication number
- JPS6222756A JPS6222756A JP60162632A JP16263285A JPS6222756A JP S6222756 A JPS6222756 A JP S6222756A JP 60162632 A JP60162632 A JP 60162632A JP 16263285 A JP16263285 A JP 16263285A JP S6222756 A JPS6222756 A JP S6222756A
- Authority
- JP
- Japan
- Prior art keywords
- perfluoro
- formula
- compound
- cyclic amine
- reaction
- 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
- 229920002554 vinyl polymer Polymers 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
- 239000000126 substance Substances 0.000 claims abstract description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 150000001340 alkali metals Chemical group 0.000 claims abstract description 4
- 229910052784 alkaline earth metal Chemical group 0.000 claims abstract description 4
- 150000001342 alkaline earth metals Chemical group 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract 3
- 229920001774 Perfluoroether Polymers 0.000 claims abstract 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical class NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 21
- 150000001875 compounds Chemical class 0.000 abstract description 18
- 238000000034 method Methods 0.000 abstract description 11
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract description 10
- 239000011737 fluorine Substances 0.000 abstract description 10
- 239000004094 surface-active agent Substances 0.000 abstract description 4
- 238000003682 fluorination reaction Methods 0.000 abstract description 3
- 239000007858 starting material Substances 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 20
- -1 olefin compounds Chemical class 0.000 description 16
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 238000005979 thermal decomposition reaction Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- AGOSBLVKCWSMAB-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6-decafluoro-1-(1,2,2-trifluoroethenyl)piperidine Chemical compound FC(F)=C(F)N1C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F AGOSBLVKCWSMAB-UHFFFAOYSA-N 0.000 description 5
- DURDQXXTRHKVCX-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluoro-1-(1,2,2-trifluoroethenyl)pyrrolidine Chemical compound FC(F)=C(F)N1C(F)(F)C(F)(F)C(F)(F)C1(F)F DURDQXXTRHKVCX-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 229910052734 helium Inorganic materials 0.000 description 5
- 239000001307 helium Substances 0.000 description 5
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- IRALJUDAKKIPMS-UHFFFAOYSA-N 3,3,3-trifluoro-2-(2,2,3,3,4,4,5,5-octafluoropyrrolidin-1-yl)-2-(trifluoromethyl)propanoic acid Chemical compound OC(=O)C(C(F)(F)F)(C(F)(F)F)N1C(F)(F)C(F)(F)C(F)(F)C1(F)F IRALJUDAKKIPMS-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- GTPQFCOJHZQXRX-UHFFFAOYSA-N FC(=O)C(C)N1CCCC1 Chemical compound FC(=O)C(C)N1CCCC1 GTPQFCOJHZQXRX-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- VCEAGMYKGZNUFL-UHFFFAOYSA-N 1,2,2,3,3,4,4,5,5,6,6-undecafluoropiperidine Chemical compound FN1C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F VCEAGMYKGZNUFL-UHFFFAOYSA-N 0.000 description 3
- FYWMUSXBRBQLJG-UHFFFAOYSA-N 2,2,3,3,5,5,6,6-octafluoro-4-(1,2,2-trifluoroethenyl)morpholine Chemical compound FC(F)=C(F)N1C(F)(F)C(F)(F)OC(F)(F)C1(F)F FYWMUSXBRBQLJG-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- BCYHICYAWLIZRU-UHFFFAOYSA-N methyl 2-pyrrolidin-1-ylpropanoate Chemical compound COC(=O)C(C)N1CCCC1 BCYHICYAWLIZRU-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- XOVVBNBRQKDYIF-UHFFFAOYSA-N 2,2,3,3,5,5,6,6-octafluoro-1-(1,1,2,2,2-pentafluoroethyl)-4-(1,2,2-trifluoroethenyl)piperazine Chemical compound FC(F)=C(F)N1C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)F)C(F)(F)C1(F)F XOVVBNBRQKDYIF-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000005796 dehydrofluorination reaction Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229940017219 methyl propionate Drugs 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- WZASSYDMYUZHRC-UHFFFAOYSA-N 1,2,2-trifluoro-n,n-bis(trifluoromethyl)ethenamine Chemical compound FC(F)=C(F)N(C(F)(F)F)C(F)(F)F WZASSYDMYUZHRC-UHFFFAOYSA-N 0.000 description 1
- LEWNYOKWUAYXPI-UHFFFAOYSA-N 1-ethenylpiperidine Chemical compound C=CN1CCCCC1 LEWNYOKWUAYXPI-UHFFFAOYSA-N 0.000 description 1
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 1
- LRMSQVBRUNSOJL-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)F LRMSQVBRUNSOJL-UHFFFAOYSA-N 0.000 description 1
- UMGCTGRNIYHTCR-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluoro-1-(1,1,2,2,2-pentafluoroethyl)pyrrolidine Chemical compound FC(F)(F)C(F)(F)N1C(F)(F)C(F)(F)C(F)(F)C1(F)F UMGCTGRNIYHTCR-UHFFFAOYSA-N 0.000 description 1
- LIJRSRSBXLWJIJ-UHFFFAOYSA-N 2-morpholin-4-ylpropanoyl fluoride Chemical compound FC(=O)C(C)N1CCOCC1 LIJRSRSBXLWJIJ-UHFFFAOYSA-N 0.000 description 1
- MTSISEQPNWCDIY-UHFFFAOYSA-N 4-fluoromorpholine Chemical compound FN1CCOCC1 MTSISEQPNWCDIY-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CXKCTMHTOKXKQT-UHFFFAOYSA-N cadmium oxide Inorganic materials [Cd]=O CXKCTMHTOKXKQT-UHFFFAOYSA-N 0.000 description 1
- CFEAAQFZALKQPA-UHFFFAOYSA-N cadmium(2+);oxygen(2-) Chemical compound [O-2].[Cd+2] CFEAAQFZALKQPA-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- SUTVUAKNYMVZEL-UHFFFAOYSA-N n,n,1,2,2-pentafluoroethenamine Chemical class FN(F)C(F)=C(F)F SUTVUAKNYMVZEL-UHFFFAOYSA-N 0.000 description 1
- USAAEUHMVCSUQS-UHFFFAOYSA-N perfluoro-N-ethylpiperidine Chemical compound FC(F)(F)C(F)(F)N1C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F USAAEUHMVCSUQS-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- WMFABESKCHGSRC-UHFFFAOYSA-N propanoyl fluoride Chemical compound CCC(F)=O WMFABESKCHGSRC-UHFFFAOYSA-N 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- Y02P20/121—
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60162632A JPS6222756A (ja) | 1985-07-23 | 1985-07-23 | 新規なペルフルオロ（ｎ−ビニル環状アミン）の製造方法 |
| US06/886,608 US4782148A (en) | 1985-07-23 | 1986-07-18 | Method for production of perfluoro N-(vinyl)amines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60162632A JPS6222756A (ja) | 1985-07-23 | 1985-07-23 | 新規なペルフルオロ（ｎ−ビニル環状アミン）の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6222756A true JPS6222756A (ja) | 1987-01-30 |
| JPS638102B2 JPS638102B2 (enrdf_load_stackoverflow) | 1988-02-19 |
Family
ID=15758299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60162632A Granted JPS6222756A (ja) | 1985-07-23 | 1985-07-23 | 新規なペルフルオロ（ｎ−ビニル環状アミン）の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6222756A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6470444A (en) * | 1987-09-10 | 1989-03-15 | Agency Ind Science Techn | Novel perfluoroalkenylamine and production thereof |
| JPS6470443A (en) * | 1987-09-10 | 1989-03-15 | Agency Ind Science Techn | Novel nitrogen-containing perfluoropropenes and production thereof |
| US4912216A (en) * | 1986-07-15 | 1990-03-27 | Agency Of Industrial Science & Technology | Method for production of perfluoro-(N-vinylamine) compounds |
| US4985556A (en) * | 1987-09-10 | 1991-01-15 | Agency Of Industrial Science & Technology | Perfluoro(dialkylaminopropene) derivatives |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63112908U (enrdf_load_stackoverflow) * | 1987-01-19 | 1988-07-20 | ||
| JPH0324406U (enrdf_load_stackoverflow) * | 1989-07-13 | 1991-03-13 |
-
1985
- 1985-07-23 JP JP60162632A patent/JPS6222756A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4912216A (en) * | 1986-07-15 | 1990-03-27 | Agency Of Industrial Science & Technology | Method for production of perfluoro-(N-vinylamine) compounds |
| JPS6470444A (en) * | 1987-09-10 | 1989-03-15 | Agency Ind Science Techn | Novel perfluoroalkenylamine and production thereof |
| JPS6470443A (en) * | 1987-09-10 | 1989-03-15 | Agency Ind Science Techn | Novel nitrogen-containing perfluoropropenes and production thereof |
| US4985556A (en) * | 1987-09-10 | 1991-01-15 | Agency Of Industrial Science & Technology | Perfluoro(dialkylaminopropene) derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS638102B2 (enrdf_load_stackoverflow) | 1988-02-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |