CA2871328C - Methods for producing 1,5,7-triazabicyclo[4.4.0]dec-5-ene by reaction of a disubstituted carbodiimide and dipropylene triamine - Google Patents
Methods for producing 1,5,7-triazabicyclo[4.4.0]dec-5-ene by reaction of a disubstituted carbodiimide and dipropylene triamine Download PDFInfo
- Publication number
- CA2871328C CA2871328C CA2871328A CA2871328A CA2871328C CA 2871328 C CA2871328 C CA 2871328C CA 2871328 A CA2871328 A CA 2871328A CA 2871328 A CA2871328 A CA 2871328A CA 2871328 C CA2871328 C CA 2871328C
- Authority
- CA
- Canada
- Prior art keywords
- ene
- dec
- triazabicyclo
- dipropylene triamine
- disubstituted carbodiimide
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title claims abstract description 46
- 150000001718 carbodiimides Chemical class 0.000 title claims abstract description 37
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical class CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 title claims abstract description 35
- FVKFHMNJTHKMRX-UHFFFAOYSA-N 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine Chemical compound C1CCN2CCCNC2=N1 FVKFHMNJTHKMRX-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000006243 chemical reaction Methods 0.000 title claims description 54
- 239000002904 solvent Substances 0.000 claims abstract description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000008199 coating composition Substances 0.000 claims abstract description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 42
- -1 hexaethoxylated bisphenol A polyol Chemical class 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 18
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 15
- 229920005862 polyol Polymers 0.000 claims description 13
- 239000006227 byproduct Substances 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 5
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 claims description 5
- BOSWPVRACYJBSJ-UHFFFAOYSA-N 1,3-di(p-tolyl)carbodiimide Chemical compound C1=CC(C)=CC=C1N=C=NC1=CC=C(C)C=C1 BOSWPVRACYJBSJ-UHFFFAOYSA-N 0.000 claims description 3
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims description 3
- 239000000758 substrate Substances 0.000 abstract 2
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 238000001652 electrophoretic deposition Methods 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000004821 distillation Methods 0.000 description 13
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical group NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 10
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- WYMDDFRYORANCC-UHFFFAOYSA-N 2-[[3-[bis(carboxymethyl)amino]-2-hydroxypropyl]-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)CN(CC(O)=O)CC(O)=O WYMDDFRYORANCC-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- UURSXESKOOOTOV-UHFFFAOYSA-N dec-5-ene Chemical compound CCCCC=CCCCC UURSXESKOOOTOV-UHFFFAOYSA-N 0.000 description 5
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- QEJORCUFWWJJPP-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO.CCCCOCCO QEJORCUFWWJJPP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 231100001261 hazardous Toxicity 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- DKWHHTWSTXZKDW-UHFFFAOYSA-N 1-[2-[2-[2-(2-butoxyethoxy)ethoxymethoxy]ethoxy]ethoxy]butane Chemical compound CCCCOCCOCCOCOCCOCCOCCCC DKWHHTWSTXZKDW-UHFFFAOYSA-N 0.000 description 1
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- GTYXGPZGVCNWBM-UHFFFAOYSA-N C=CC.C=CC.C1(=CC=C(C=C1)N=C=NC1=CC=C(C=C1)C)C Chemical group C=CC.C=CC.C1(=CC=C(C=C1)N=C=NC1=CC=C(C=C1)C)C GTYXGPZGVCNWBM-UHFFFAOYSA-N 0.000 description 1
- ACHGVDLUXVYSDQ-UHFFFAOYSA-N C=CC.C=CC.C1(CCCCC1)N=C=NC1CCCCC1 Chemical group C=CC.C=CC.C1(CCCCC1)N=C=NC1CCCCC1 ACHGVDLUXVYSDQ-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- IDVWLLCLTVBSCS-UHFFFAOYSA-N n,n'-ditert-butylmethanediimine Chemical compound CC(C)(C)N=C=NC(C)(C)C IDVWLLCLTVBSCS-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 238000012306 spectroscopic technique Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229940055764 triaz Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
- Paints Or Removers (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/455,651 US9108968B2 (en) | 2012-04-25 | 2012-04-25 | Methods for producing 1,5,7-triazabicyclo[4.4.0]dec-5-ene by reaction of a disubstituted carbodiimide and dipropylene triamine |
| US13/455,651 | 2012-04-25 | ||
| US13/780,469 US20130289273A1 (en) | 2012-04-25 | 2013-02-28 | Methods for producing 1,5,7-triazabicyclo[4.4.0]dec-5-ene by reaction of a disubstituted carbodiimide and dipropylene triamine |
| US13/780,469 | 2013-02-28 | ||
| PCT/US2013/037713 WO2013163130A1 (en) | 2012-04-25 | 2013-04-23 | Methods for producing 1,5,7-triazabicyclo[4.4.0] dec-5-ene by reaction of a disubstituted carbodiimide and dipropylene triamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2871328A1 CA2871328A1 (en) | 2013-10-31 |
| CA2871328C true CA2871328C (en) | 2017-10-03 |
Family
ID=48225149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2871328A Active CA2871328C (en) | 2012-04-25 | 2013-04-23 | Methods for producing 1,5,7-triazabicyclo[4.4.0]dec-5-ene by reaction of a disubstituted carbodiimide and dipropylene triamine |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20130289273A1 (https=) |
| EP (1) | EP2841436B1 (https=) |
| KR (1) | KR101684044B1 (https=) |
| CN (2) | CN104254536B (https=) |
| CA (1) | CA2871328C (https=) |
| ES (1) | ES2644284T3 (https=) |
| HK (1) | HK1202871A1 (https=) |
| HU (1) | HUE037194T2 (https=) |
| IN (1) | IN2014DN08729A (https=) |
| MX (1) | MX351408B (https=) |
| PL (1) | PL2841436T3 (https=) |
| RU (1) | RU2600741C2 (https=) |
| WO (1) | WO2013163130A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201434882A (zh) * | 2013-03-13 | 2014-09-16 | Momentive Performance Mat Inc | 可濕氣固化之有機聚矽氧烷組成物 |
| US9688874B2 (en) | 2013-10-25 | 2017-06-27 | Ppg Industries Ohio, Inc. | Method of making a bicyclic guanidine-cured acrylic coating |
| WO2015158864A1 (de) * | 2014-04-16 | 2015-10-22 | Sika Technology Ag | Amidin - oder guanidingruppen-haltiges silan |
| FI129024B (en) | 2017-11-08 | 2021-05-14 | Helsingin Yliopisto | Process for the preparation of bicyclic guanidine and its derivatives |
| US12145937B2 (en) * | 2018-09-06 | 2024-11-19 | Wacker Chemie Ag | Process for preparing bicyclic guanidines |
| CN119751458A (zh) * | 2024-11-15 | 2025-04-04 | 清华大学 | 环氧树脂潜伏固化促进剂及其制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7842762B2 (en) * | 2007-08-08 | 2010-11-30 | Ppg Industries Ohio, Inc. | Electrodepositable coating composition containing a cyclic guanidine |
| CN102665406B (zh) | 2009-12-24 | 2016-03-09 | 诺沃梅尔公司 | 合成多环胍化合物的方法 |
| US8148490B2 (en) * | 2010-03-10 | 2012-04-03 | Ppg Industries Ohio, Inc. | Method of making a cyclic guanidine from a guanidinium salt and a weak acid and coating compositions containing the same |
| US8563560B2 (en) | 2011-02-25 | 2013-10-22 | Ppg Industries Ohio, Inc. | Preparation of bicyclic guanidine salts in an aqueous media |
-
2013
- 2013-02-28 US US13/780,469 patent/US20130289273A1/en not_active Abandoned
- 2013-04-23 RU RU2014147324/04A patent/RU2600741C2/ru active
- 2013-04-23 CA CA2871328A patent/CA2871328C/en active Active
- 2013-04-23 WO PCT/US2013/037713 patent/WO2013163130A1/en not_active Ceased
- 2013-04-23 PL PL13719358T patent/PL2841436T3/pl unknown
- 2013-04-23 EP EP13719358.7A patent/EP2841436B1/en active Active
- 2013-04-23 CN CN201380021646.1A patent/CN104254536B/zh active Active
- 2013-04-23 MX MX2014012932A patent/MX351408B/es active IP Right Grant
- 2013-04-23 IN IN8729DEN2014 patent/IN2014DN08729A/en unknown
- 2013-04-23 HK HK15103448.5A patent/HK1202871A1/xx unknown
- 2013-04-23 CN CN201610981485.6A patent/CN106518881B/zh active Active
- 2013-04-23 KR KR1020147029687A patent/KR101684044B1/ko active Active
- 2013-04-23 ES ES13719358.7T patent/ES2644284T3/es active Active
- 2013-04-23 HU HUE13719358A patent/HUE037194T2/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IN2014DN08729A (https=) | 2015-05-22 |
| WO2013163130A1 (en) | 2013-10-31 |
| RU2600741C2 (ru) | 2016-10-27 |
| MX2014012932A (es) | 2015-02-10 |
| PL2841436T3 (pl) | 2018-01-31 |
| CA2871328A1 (en) | 2013-10-31 |
| EP2841436A1 (en) | 2015-03-04 |
| RU2014147324A (ru) | 2016-06-10 |
| KR20140139579A (ko) | 2014-12-05 |
| MX351408B (es) | 2017-10-12 |
| US20130289273A1 (en) | 2013-10-31 |
| HK1202871A1 (en) | 2015-10-09 |
| ES2644284T3 (es) | 2017-11-28 |
| KR101684044B1 (ko) | 2016-12-07 |
| CN104254536A (zh) | 2014-12-31 |
| CN104254536B (zh) | 2017-03-15 |
| HUE037194T2 (hu) | 2018-08-28 |
| CN106518881A (zh) | 2017-03-22 |
| EP2841436B1 (en) | 2017-08-23 |
| CN106518881B (zh) | 2018-11-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20141022 |