NZ272305A - Diamine derivatives - Google Patents
Diamine derivativesInfo
- Publication number
- NZ272305A NZ272305A NZ272305A NZ27230592A NZ272305A NZ 272305 A NZ272305 A NZ 272305A NZ 272305 A NZ272305 A NZ 272305A NZ 27230592 A NZ27230592 A NZ 27230592A NZ 272305 A NZ272305 A NZ 272305A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- morpholino
- diethyl ether
- ring
- azoniaspiro
- Prior art date
Links
- 150000004985 diamines Chemical class 0.000 title claims abstract description 18
- 150000003335 secondary amines Chemical class 0.000 claims abstract description 9
- 125000003003 spiro group Chemical group 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 30
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 22
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 11
- PVASRWDJQIBGKC-UHFFFAOYSA-M 3,9-dioxa-6-azoniaspiro[5.5]undecane;chloride Chemical compound [Cl-].C1COCC[N+]21CCOCC2 PVASRWDJQIBGKC-UHFFFAOYSA-M 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 claims description 6
- -1 hexamethyleneimino Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical compound CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 claims description 3
- MNWMYQXWKRLNLC-UHFFFAOYSA-M [Cl-].CC1C[N+]2(CCOCC2)CC(O1)C Chemical compound [Cl-].CC1C[N+]2(CCOCC2)CC(O1)C MNWMYQXWKRLNLC-UHFFFAOYSA-M 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- LKNYSEBKSZTLBV-UHFFFAOYSA-M 10-methyl-3-oxa-6-azoniaspiro[5.5]undecane;chloride Chemical compound [Cl-].C1C(C)CCC[N+]11CCOCC1 LKNYSEBKSZTLBV-UHFFFAOYSA-M 0.000 claims description 2
- JCCCMQIEVIJZHZ-UHFFFAOYSA-M 3-oxa-6-azoniaspiro[5.5]undecane;chloride Chemical compound [Cl-].C1CCCC[N+]21CCOCC2 JCCCMQIEVIJZHZ-UHFFFAOYSA-M 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 9
- 239000004599 antimicrobial Substances 0.000 abstract description 2
- 150000001412 amines Chemical group 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000007788 liquid Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 239000000543 intermediate Substances 0.000 description 13
- 238000002156 mixing Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 11
- 229960004132 diethyl ether Drugs 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 241000195652 Auxenochlorella pyrenoidosa Species 0.000 description 3
- 235000007091 Chlorella pyrenoidosa Nutrition 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000588915 Klebsiella aerogenes Species 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000000526 short-path distillation Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- ZMSQJSMSLXVTKN-UHFFFAOYSA-N 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine Chemical compound C1COCCN1CCOCCN1CCOCC1 ZMSQJSMSLXVTKN-UHFFFAOYSA-N 0.000 description 2
- 241000195493 Cryptophyta Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229940092559 enterobacter aerogenes Drugs 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 150000003413 spiro compounds Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OADNVNPVQYWJMK-UHFFFAOYSA-N undecane;hydrochloride Chemical compound Cl.CCCCCCCCCCC OADNVNPVQYWJMK-UHFFFAOYSA-N 0.000 description 2
- LBKDGROORAKTLC-UHFFFAOYSA-N 1,5-dichloropentane Chemical compound ClCCCCCCl LBKDGROORAKTLC-UHFFFAOYSA-N 0.000 description 1
- UFLFSJVTFSZTKX-UHFFFAOYSA-N 2,2-dimethylmorpholine Chemical compound CC1(C)CNCCO1 UFLFSJVTFSZTKX-UHFFFAOYSA-N 0.000 description 1
- FYELSNVLZVIGTI-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-5-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1CC)CC(=O)N1CC2=C(CC1)NN=N2 FYELSNVLZVIGTI-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- AFBCNGAMDTUIBQ-UHFFFAOYSA-M [Cl-].CC1CC[N+]2(CC1)CCC(CC2)C Chemical compound [Cl-].CC1CC[N+]2(CC1)CCC(CC2)C AFBCNGAMDTUIBQ-UHFFFAOYSA-M 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2009—Heterocyclic amines; Salts thereof containing one heterocyclic ring
- C08G18/2018—Heterocyclic amines; Salts thereof containing one heterocyclic ring having one nitrogen atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2009—Heterocyclic amines; Salts thereof containing one heterocyclic ring
- C08G18/2027—Heterocyclic amines; Salts thereof containing one heterocyclic ring having two nitrogen atoms in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2081—Heterocyclic amines; Salts thereof containing at least two non-condensed heterocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Polyurethanes Or Polyureas (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/728,688 US5268470A (en) | 1991-07-12 | 1991-07-12 | Diamine compounds, method of making same, method of use of same and intermediates |
| NZ243536A NZ243536A (en) | 1991-07-12 | 1992-07-13 | Spiroquaternary ammonium compounds and antimicrobial agents thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ272305A true NZ272305A (en) | 1995-11-27 |
Family
ID=24927902
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ272305A NZ272305A (en) | 1991-07-12 | 1992-07-13 | Diamine derivatives |
| NZ243536A NZ243536A (en) | 1991-07-12 | 1992-07-13 | Spiroquaternary ammonium compounds and antimicrobial agents thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ243536A NZ243536A (en) | 1991-07-12 | 1992-07-13 | Spiroquaternary ammonium compounds and antimicrobial agents thereof |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US5268470A (enExample) |
| EP (2) | EP0594715B1 (enExample) |
| JP (1) | JPH07502259A (enExample) |
| AT (1) | ATE139228T1 (enExample) |
| AU (1) | AU653304B2 (enExample) |
| BR (1) | BR9206268A (enExample) |
| CA (1) | CA2113189C (enExample) |
| DE (1) | DE69211555T2 (enExample) |
| DK (1) | DK0594715T3 (enExample) |
| ES (1) | ES2089541T3 (enExample) |
| FI (1) | FI106859B (enExample) |
| GR (1) | GR3020699T3 (enExample) |
| MX (1) | MX9204080A (enExample) |
| NO (1) | NO305700B1 (enExample) |
| NZ (2) | NZ272305A (enExample) |
| WO (1) | WO1993001178A1 (enExample) |
| ZA (1) | ZA925207B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996033986A1 (de) * | 1995-04-26 | 1996-10-31 | Lonza Ag | Piperidinpentanamine, verfahren zu ihrer herstellung und verwendung als katalysator bei der herstellung von urethanen |
| DE19742720A1 (de) * | 1997-09-26 | 1999-04-01 | Performance Chemicals Handels | Bis(alkylamino)alkylether-Verbindungen und ihre Verwendung |
| US20030151159A1 (en) * | 2001-09-28 | 2003-08-14 | Jorge Santisteban | Protective composite wrap |
| US8501828B2 (en) * | 2004-08-11 | 2013-08-06 | Huntsman Petrochemical Llc | Cure rebond binder |
| US20060141239A1 (en) * | 2004-12-28 | 2006-06-29 | Gilder Stephen D | Method for making a bonded foam product suitable for use as an underlayment for floor coverings |
| DE102014215388A1 (de) | 2014-08-05 | 2016-02-11 | Evonik Degussa Gmbh | Stickstoffhaltige Verbindungen, geeignet zur Verwendung bei der Herstellung von Polyurethanen |
| US10633355B2 (en) | 2014-12-04 | 2020-04-28 | Uop Llc | Organo-1-oxa-4-azonium cyclohexane compounds |
| US10597373B2 (en) | 2014-12-04 | 2020-03-24 | Uop Llc | Organo-1-oxa-4-azonium cyclohexane compounds |
| US10654817B2 (en) | 2014-12-04 | 2020-05-19 | Uop Llc | Organo-1-oxa-4-azonium cyclohexane compounds |
| US9522896B2 (en) * | 2014-12-04 | 2016-12-20 | Uop Llc | Organo-1-oxa-4-azonium cyclohexane compounds |
| JP7153561B2 (ja) * | 2016-03-28 | 2022-10-14 | ユニバーシティー オブ デラウェア | ヒドロキシド交換膜およびヒドロキシド交換アイオノマーとしての使用のためのポリ（アリールピペリジニウム）ポリマー |
| WO2019068051A2 (en) * | 2017-09-28 | 2019-04-04 | Yushan Yan | POLY (ARYL PIPERIDINIUM) POLYMERS COMPRISING THOSE HAVING STATIC CATIONIC PENDANT GROUPS FOR USE AS ANION AND IONOMER EXCHANGING MEMBRANES |
| ES3040095T3 (en) | 2019-03-28 | 2025-10-28 | Univ Delaware | Polymers having stable cationic pendant groups for use as anion exchange membranes |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB781407A (en) * | 1955-10-14 | 1957-08-21 | Sapos Lab | New quaternary amino ethers |
| US3366631A (en) * | 1959-04-03 | 1968-01-30 | Searle & Co | 4-(lower alkyl)-3-methyl-2-cycloalkyl-morpholines and congeners |
| US3619221A (en) * | 1970-03-25 | 1971-11-09 | Grace W R & Co | Amine formate accelerator additives for portland cement compositions |
| DE2624016C2 (de) * | 1975-06-02 | 1987-04-23 | Texaco Development Corp., White Plains, N.Y. | Verfahren zur Herstellung von Bis-(morpholino-N-alkyl)äthern |
| US4117227A (en) * | 1975-06-02 | 1978-09-26 | Texaco Development Corp. | Production of n-(substituted) morpholine |
| US4026935A (en) * | 1975-06-02 | 1977-05-31 | Texaco Development Corporation | Production of bis-(morpholino-N-alkyl) ethers |
| US4113709A (en) * | 1976-08-12 | 1978-09-12 | Petrolite Corporation | Polyquaternary polythiazines |
| CA1117552A (en) * | 1977-12-27 | 1982-02-02 | Fedor Poppelsdorf | Process for producing bis(n,n-dialkylamino) alkyl ethers |
| SE448538B (sv) * | 1979-03-30 | 1987-03-02 | Union Carbide Corp | Forfarande for framstellning av bis-(n,n-dialkylamino)alkyletrar |
| DE3143706A1 (de) * | 1981-11-04 | 1983-05-11 | Bayer Ag, 5090 Leverkusen | Hochfrequenzverschweissbare polyurethanschaumstoffe und ein verfahren zur herstellung derselben |
| US4574793A (en) * | 1984-08-21 | 1986-03-11 | Hexcel Corporation | Stabilized, catalyzed water activated polyurethane systems |
| US4785127A (en) * | 1985-08-05 | 1988-11-15 | Arco Chemical Company | Vinyl polymer polyols made using partially alkoxylated polyoxyalkyleneamines |
| JPH078982B2 (ja) * | 1989-05-25 | 1995-02-01 | サンスター技研株式会社 | 湿気硬化性シーリング材組成物 |
| US5214142A (en) * | 1990-09-20 | 1993-05-25 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for the preparation of aminoethers |
-
1991
- 1991-07-12 US US07/728,688 patent/US5268470A/en not_active Expired - Lifetime
-
1992
- 1992-07-08 AU AU22999/92A patent/AU653304B2/en not_active Ceased
- 1992-07-08 ES ES92915345T patent/ES2089541T3/es not_active Expired - Lifetime
- 1992-07-08 DK DK92915345.0T patent/DK0594715T3/da active
- 1992-07-08 BR BR9206268A patent/BR9206268A/pt not_active IP Right Cessation
- 1992-07-08 CA CA002113189A patent/CA2113189C/en not_active Expired - Fee Related
- 1992-07-08 EP EP92915345A patent/EP0594715B1/en not_active Expired - Lifetime
- 1992-07-08 EP EP95203308A patent/EP0705825A2/en not_active Withdrawn
- 1992-07-08 DE DE69211555T patent/DE69211555T2/de not_active Expired - Fee Related
- 1992-07-08 WO PCT/US1992/005574 patent/WO1993001178A1/en not_active Ceased
- 1992-07-08 JP JP5502322A patent/JPH07502259A/ja active Pending
- 1992-07-08 AT AT92915345T patent/ATE139228T1/de not_active IP Right Cessation
- 1992-07-10 MX MX9204080A patent/MX9204080A/es not_active IP Right Cessation
- 1992-07-13 NZ NZ272305A patent/NZ272305A/en not_active IP Right Cessation
- 1992-07-13 NZ NZ243536A patent/NZ243536A/en not_active IP Right Cessation
- 1992-07-13 ZA ZA925207A patent/ZA925207B/xx unknown
-
1993
- 1993-11-05 US US08/147,410 patent/US5869655A/en not_active Expired - Fee Related
-
1994
- 1994-01-11 FI FI940118A patent/FI106859B/fi not_active IP Right Cessation
- 1994-01-11 NO NO940094A patent/NO305700B1/no not_active IP Right Cessation
-
1996
- 1996-07-31 GR GR960402067T patent/GR3020699T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO940094L (no) | 1994-01-11 |
| FI940118A0 (fi) | 1994-01-11 |
| EP0594715B1 (en) | 1996-06-12 |
| US5869655A (en) | 1999-02-09 |
| ZA925207B (en) | 1993-04-28 |
| AU2299992A (en) | 1993-02-11 |
| BR9206268A (pt) | 1995-04-11 |
| ATE139228T1 (de) | 1996-06-15 |
| NO940094D0 (no) | 1994-01-11 |
| ES2089541T3 (es) | 1996-10-01 |
| DK0594715T3 (da) | 1996-07-29 |
| CA2113189C (en) | 2001-10-30 |
| FI106859B (fi) | 2001-04-30 |
| US5268470A (en) | 1993-12-07 |
| CA2113189A1 (en) | 1993-01-21 |
| AU653304B2 (en) | 1994-09-22 |
| MX9204080A (es) | 1993-08-01 |
| DE69211555T2 (de) | 1997-01-02 |
| GR3020699T3 (en) | 1996-10-31 |
| NZ243536A (en) | 1995-11-27 |
| WO1993001178A1 (en) | 1993-01-21 |
| NO305700B1 (no) | 1999-07-12 |
| EP0705825A3 (enExample) | 1996-04-24 |
| EP0594715A1 (en) | 1994-05-04 |
| DE69211555D1 (de) | 1996-07-18 |
| FI940118L (fi) | 1994-01-11 |
| JPH07502259A (ja) | 1995-03-09 |
| EP0705825A2 (en) | 1996-04-10 |
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| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) | ||
| EXPY | Patent expired |