JP2808489B2 - 水溶性二酸化チオ尿素誘導体及びその製造方法 - Google Patents
水溶性二酸化チオ尿素誘導体及びその製造方法Info
- Publication number
- JP2808489B2 JP2808489B2 JP2325432A JP32543290A JP2808489B2 JP 2808489 B2 JP2808489 B2 JP 2808489B2 JP 2325432 A JP2325432 A JP 2325432A JP 32543290 A JP32543290 A JP 32543290A JP 2808489 B2 JP2808489 B2 JP 2808489B2
- Authority
- JP
- Japan
- Prior art keywords
- water
- thiourea dioxide
- mol
- producing
- same
- 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
- -1 thiourea dioxide derivative Chemical class 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 title description 4
- RYYXDZDBXNUPOG-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine;dihydrochloride Chemical compound Cl.Cl.C1C(N)CCC2=C1SC(N)=N2 RYYXDZDBXNUPOG-UHFFFAOYSA-N 0.000 claims description 13
- 150000001413 amino acids Chemical class 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 239000011591 potassium Substances 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 159000000007 calcium salts Chemical class 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 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 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- 239000004471 Glycine Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- LQZPSWMMTICWHD-UHFFFAOYSA-N 1,3-dibenzylthiourea Chemical compound C=1C=CC=CC=1CNC(=S)NCC1=CC=CC=C1 LQZPSWMMTICWHD-UHFFFAOYSA-N 0.000 description 2
- JJMDCOVWQOJGCB-UHFFFAOYSA-N 5-aminopentanoic acid Chemical compound [NH3+]CCCCC([O-])=O JJMDCOVWQOJGCB-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229940000635 beta-alanine Drugs 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical group C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- KAJICSGLHKRDLN-UHFFFAOYSA-N 1,3-dicyclohexylthiourea Chemical compound C1CCCCC1NC(=S)NC1CCCCC1 KAJICSGLHKRDLN-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- FCSHMCFRCYZTRQ-UHFFFAOYSA-N N,N'-diphenylthiourea Chemical compound C=1C=CC=CC=1NC(=S)NC1=CC=CC=C1 FCSHMCFRCYZTRQ-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- WDSSTLCJMOISES-UHFFFAOYSA-N hydrogen peroxide;iron Chemical compound [Fe].OO WDSSTLCJMOISES-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- WUWHFEHKUQVYLF-UHFFFAOYSA-M sodium;2-aminoacetate Chemical group [Na+].NCC([O-])=O WUWHFEHKUQVYLF-UHFFFAOYSA-M 0.000 description 1
- QKJPFZCCZMBRFB-UHFFFAOYSA-M sodium;3-aminopropanoate Chemical compound [Na+].NCCC([O-])=O QKJPFZCCZMBRFB-UHFFFAOYSA-M 0.000 description 1
- MJGIKHNOXNRIHX-UHFFFAOYSA-M sodium;4-aminobutanoate Chemical compound [Na+].NCCCC([O-])=O MJGIKHNOXNRIHX-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/14—Compounds containing a carbon atom having four bonds to hetero atoms with a double bond to one hetero atom and at least one bond to a sulfur atom further doubly-bound to oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2325432A JP2808489B2 (ja) | 1990-11-29 | 1990-11-29 | 水溶性二酸化チオ尿素誘導体及びその製造方法 |
| KR1019910020752A KR100197402B1 (ko) | 1990-11-29 | 1991-11-20 | 수용성 이산화티오요소 유도체 및 그의 제조방법 |
| US07/797,789 US5149871A (en) | 1990-11-29 | 1991-11-25 | Water-soluble thiourea dioxide derivatives and process for preparing same |
| EP91311047A EP0488749B1 (en) | 1990-11-29 | 1991-11-28 | Water-soluble thiourea dioxide derivatives and process for preparing same |
| DE69116829T DE69116829T2 (de) | 1990-11-29 | 1991-11-28 | Wasserlösliche Thioharnstoffdioxidderivate und Verfahren zu ihrer Herstellung |
| CA002056548A CA2056548A1 (en) | 1990-11-29 | 1991-11-28 | Water-soluble thiourea dioxide derivatives and process for preparing same |
| ES91311047T ES2082159T3 (es) | 1990-11-29 | 1991-11-28 | Derivados de tiourea hidrosolubles y procedimiento para su preparacion. |
| TW081101122A TW197417B (cg-RX-API-DMAC7.html) | 1990-11-29 | 1992-02-17 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2325432A JP2808489B2 (ja) | 1990-11-29 | 1990-11-29 | 水溶性二酸化チオ尿素誘導体及びその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04198163A JPH04198163A (ja) | 1992-07-17 |
| JP2808489B2 true JP2808489B2 (ja) | 1998-10-08 |
Family
ID=18176796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2325432A Expired - Fee Related JP2808489B2 (ja) | 1990-11-29 | 1990-11-29 | 水溶性二酸化チオ尿素誘導体及びその製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5149871A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0488749B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2808489B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR100197402B1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2056548A1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE69116829T2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2082159T3 (cg-RX-API-DMAC7.html) |
| TW (1) | TW197417B (cg-RX-API-DMAC7.html) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4319779B2 (ja) * | 2000-12-15 | 2009-08-26 | 電気化学工業株式会社 | エチレン−酢酸ビニル系共重合体エマルジョンの製造方法及びそのエマルジョン並びに接着剤組成物 |
| CN101525311B (zh) * | 2009-04-21 | 2011-10-26 | 福州大学 | 一种含磺酸基团的二氧化硫脲衍生物及其制备方法 |
| KR101853332B1 (ko) | 2015-08-03 | 2018-05-02 | (주)홍익기술단 | 하폐수 처리용 미생물 담체 제조방법 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3121111A (en) * | 1960-06-20 | 1964-02-11 | Baxter Laboratories Inc | Novel 4-thiohydantoic acids |
| JPH0296563A (ja) * | 1988-09-30 | 1990-04-09 | Tokai Denka Kogyo Kk | 二酸化チオ尿素誘導体の製造方法 |
-
1990
- 1990-11-29 JP JP2325432A patent/JP2808489B2/ja not_active Expired - Fee Related
-
1991
- 1991-11-20 KR KR1019910020752A patent/KR100197402B1/ko not_active Expired - Fee Related
- 1991-11-25 US US07/797,789 patent/US5149871A/en not_active Expired - Fee Related
- 1991-11-28 DE DE69116829T patent/DE69116829T2/de not_active Expired - Fee Related
- 1991-11-28 CA CA002056548A patent/CA2056548A1/en not_active Abandoned
- 1991-11-28 EP EP91311047A patent/EP0488749B1/en not_active Expired - Lifetime
- 1991-11-28 ES ES91311047T patent/ES2082159T3/es not_active Expired - Lifetime
-
1992
- 1992-02-17 TW TW081101122A patent/TW197417B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| US5149871A (en) | 1992-09-22 |
| JPH04198163A (ja) | 1992-07-17 |
| EP0488749B1 (en) | 1996-01-31 |
| CA2056548A1 (en) | 1992-05-30 |
| EP0488749A1 (en) | 1992-06-03 |
| TW197417B (cg-RX-API-DMAC7.html) | 1993-01-01 |
| KR100197402B1 (ko) | 1999-06-15 |
| KR920009788A (ko) | 1992-06-25 |
| ES2082159T3 (es) | 1996-03-16 |
| DE69116829D1 (de) | 1996-03-14 |
| DE69116829T2 (de) | 1996-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| LAPS | Cancellation because of no payment of annual fees |