CA1089868A - Acides amines tertiaires, nitriles amines tertiaires et sels amines d'acides amines tertiaires formant des catalyseurs a effet retarde - Google Patents

Acides amines tertiaires, nitriles amines tertiaires et sels amines d'acides amines tertiaires formant des catalyseurs a effet retarde

Info

Publication number: CA1089868A
Authority: CA; Canada
Prior art keywords: amino acid; tertiary amino; group; amine; carbon atoms
Prior art date: 1976-08-26
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

Application number

CA337,170A

Other languages

English (en)

Inventor

Ibrahim S. Bechara

Rocco L. Mascioli

Philip J. Zaluska

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Air Products and Chemicals Inc

Original Assignee

Air Products and Chemicals Inc

Priority date (The priority date 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 date listed.)

1976-08-26

Filing date

1979-10-09

Publication date

1980-11-18

1976-08-26 Priority claimed from US05/717,579 external-priority patent/US4086213A/en

1976-12-01 Priority claimed from US05/746,313 external-priority patent/US4134994A/en

1977-08-09 Priority claimed from CA284,382A external-priority patent/CA1083552A/fr

1979-10-09 Application filed by Air Products and Chemicals Inc filed Critical Air Products and Chemicals Inc

1979-10-09 Priority to CA337,170A priority Critical patent/CA1089868A/fr

1980-11-18 Application granted granted Critical

1980-11-18 Publication of CA1089868A publication Critical patent/CA1089868A/fr

Status Expired legal-status Critical Current

Links

-1 amine salts Chemical class 0.000 title claims abstract description 52
239000003054 catalyst Substances 0.000 title abstract description 60
239000000203 mixture Substances 0.000 title abstract description 56
125000001302 tertiary amino group Chemical group 0.000 title abstract description 29
230000003111 delayed effect Effects 0.000 title abstract description 20
150000002825 nitriles Chemical class 0.000 title description 10
125000000217 alkyl group Chemical group 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
125000002843 carboxylic acid group Chemical group 0.000 claims description 7
150000002431 hydrogen Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 3
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
125000002560 nitrile group Chemical group 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
229930194542 Keto Natural products 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000000468 ketone group Chemical group 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
150000001735 carboxylic acids Chemical class 0.000 claims 1
125000005270 trialkylamine group Chemical group 0.000 claims 1
239000004814 polyurethane Substances 0.000 abstract description 37
125000002524 organometallic group Chemical group 0.000 abstract description 36
229920002635 polyurethane Polymers 0.000 abstract description 34
150000001412 amines Chemical class 0.000 abstract description 30
239000002253 acid Substances 0.000 abstract description 23
230000015572 biosynthetic process Effects 0.000 abstract description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 4
238000003786 synthesis reaction Methods 0.000 abstract description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
229920005862 polyol Polymers 0.000 description 39
150000003077 polyols Chemical class 0.000 description 33
238000006243 chemical reaction Methods 0.000 description 27
235000001014 amino acid Nutrition 0.000 description 24
238000009472 formulation Methods 0.000 description 22
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 21
239000006071 cream Substances 0.000 description 21
239000012948 isocyanate Substances 0.000 description 21
150000002513 isocyanates Chemical class 0.000 description 18
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
229960005088 urethane Drugs 0.000 description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
150000001299 aldehydes Chemical class 0.000 description 11
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 11
150000003242 quaternary ammonium salts Chemical class 0.000 description 11
229920005830 Polyurethane Foam Polymers 0.000 description 10
239000011496 polyurethane foam Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
150000003512 tertiary amines Chemical class 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 8
150000001413 amino acids Chemical class 0.000 description 8
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 8
229940043237 diethanolamine Drugs 0.000 description 8
239000006188 syrup Substances 0.000 description 8
235000020357 syrup Nutrition 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
229910052751 metal Inorganic materials 0.000 description 7
239000002184 metal Substances 0.000 description 7
238000009740 moulding (composite fabrication) Methods 0.000 description 7
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 6
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 6
238000001879 gelation Methods 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 5
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
150000002894 organic compounds Chemical class 0.000 description 5
125000000962 organic group Chemical group 0.000 description 5
238000006116 polymerization reaction Methods 0.000 description 5
239000004094 surface-active agent Substances 0.000 description 5
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 5
WEJKUVSYIGOBAR-UHFFFAOYSA-N 2-morpholin-4-ium-4-ylpropanoate Chemical compound OC(=O)C(C)N1CCOCC1 WEJKUVSYIGOBAR-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
230000002411 adverse Effects 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
238000006555 catalytic reaction Methods 0.000 description 4
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
230000002708 enhancing effect Effects 0.000 description 4
229940031098 ethanolamine Drugs 0.000 description 4
238000000034 method Methods 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
229920001296 polysiloxane Polymers 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
ORARIPAOHXQIRI-UHFFFAOYSA-N 2-methyl-2-piperidin-1-ylpropanedioic acid Chemical compound OC(=O)C(C(O)=O)(C)N1CCCCC1 ORARIPAOHXQIRI-UHFFFAOYSA-N 0.000 description 3
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
239000004604 Blowing Agent Substances 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
229930006000 Sucrose Natural products 0.000 description 3
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000003431 cross linking reagent Substances 0.000 description 3
239000006260 foam Substances 0.000 description 3
229960004279 formaldehyde Drugs 0.000 description 3
235000019256 formaldehyde Nutrition 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
150000002334 glycols Chemical class 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
238000000465 moulding Methods 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000005720 sucrose Substances 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 2
WKXXOZIMRTZAHO-UHFFFAOYSA-N 2-cyano-2-morpholin-4-yl-3-phenylpropanoic acid Chemical compound C1COCCN1C(C(=O)O)(C#N)CC1=CC=CC=C1 WKXXOZIMRTZAHO-UHFFFAOYSA-N 0.000 description 2
RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical class COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 2
ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-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
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
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KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 2
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CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
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125000003545 alkoxy group Chemical group 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
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230000005494 condensation Effects 0.000 description 2
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238000010168 coupling process Methods 0.000 description 2
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JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 2
229940099364 dichlorofluoromethane Drugs 0.000 description 2
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238000001914 filtration Methods 0.000 description 2
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230000000977 initiatory effect Effects 0.000 description 2
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150000003254 radicals Chemical class 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
239000000243 solution Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
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JAEJSNFTJMYIEF-UHFFFAOYSA-N 2-benzylpropanedioic acid Chemical compound OC(=O)C(C(O)=O)CC1=CC=CC=C1 JAEJSNFTJMYIEF-UHFFFAOYSA-N 0.000 description 1
BMGFZXPTNVARBF-UHFFFAOYSA-N 2-formylfuran-3-carbonitrile Chemical compound O=CC=1OC=CC=1C#N BMGFZXPTNVARBF-UHFFFAOYSA-N 0.000 description 1
WLDIZRALGAOEAM-UHFFFAOYSA-N 2-methyl-2-morpholin-4-ylpropanedioic acid Chemical compound OC(=O)C(C(O)=O)(C)N1CCOCC1 WLDIZRALGAOEAM-UHFFFAOYSA-N 0.000 description 1
CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 1
TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 description 1
ZSIRWYMANRZZPE-UHFFFAOYSA-N 3-[bis(2-hydroxyethyl)amino]propanenitrile Chemical compound OCCN(CCO)CCC#N ZSIRWYMANRZZPE-UHFFFAOYSA-N 0.000 description 1
PZIHLHOKXFDCIZ-UHFFFAOYSA-N 3-piperidin-1-yl-2-(piperidin-1-ylmethyl)propanoic acid Chemical compound C1CCCCN1CC(C(=O)O)CN1CCCCC1 PZIHLHOKXFDCIZ-UHFFFAOYSA-N 0.000 description 1
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JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
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WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
150000003956 methylamines Chemical class 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
ZIYVHBGGAOATLY-UHFFFAOYSA-N methylmalonic acid Chemical compound OC(=O)C(C)C(O)=O ZIYVHBGGAOATLY-UHFFFAOYSA-N 0.000 description 1
229940113083 morpholine Drugs 0.000 description 1
125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
HVAAHUDGWQAAOJ-UHFFFAOYSA-N n-benzylethanamine Chemical class CCNCC1=CC=CC=C1 HVAAHUDGWQAAOJ-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000002245 particle Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920005906 polyester polyol Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001228 polyisocyanate Polymers 0.000 description 1
239000005056 polyisocyanate Substances 0.000 description 1
229920005996 polystyrene-poly(ethylene-butylene)-polystyrene Polymers 0.000 description 1
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150000003152 propanolamines Chemical class 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
UPCXAARSWVHVLY-UHFFFAOYSA-N tris(2-hydroxyethyl)azanium;acetate Chemical compound CC(O)=O.OCCN(CCO)CCO UPCXAARSWVHVLY-UHFFFAOYSA-N 0.000 description 1
OECBPUHKHTYFET-UHFFFAOYSA-J tris(decanoyloxy)stannyl decanoate Chemical compound [Sn+4].CCCCCCCCCC([O-])=O.CCCCCCCCCC([O-])=O.CCCCCCCCCC([O-])=O.CCCCCCCCCC([O-])=O OECBPUHKHTYFET-UHFFFAOYSA-J 0.000 description 1
229960004418 trolamine Drugs 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Polyurethanes Or Polyureas (AREA)

CA337,170A 1976-08-26 1979-10-09 Acides amines tertiaires, nitriles amines tertiaires et sels amines d'acides amines tertiaires formant des catalyseurs a effet retarde Expired CA1089868A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA337,170A CA1089868A (fr)	1976-08-26	1979-10-09	Acides amines tertiaires, nitriles amines tertiaires et sels amines d'acides amines tertiaires formant des catalyseurs a effet retarde

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US717,579		1976-08-26
US05/717,579 US4086213A (en)	1976-08-26	1976-08-26	Tertiary amino acid and tertiary amino acid-nitrile delayed action catalyst compositions
US05/746,313 US4134994A (en)	1976-12-01	1976-12-01	Amine salts of tertiary amino acids
US746,313		1976-12-01
CA284,382A CA1083552A (fr)	1976-08-26	1977-08-09	Catalyseurs a effet retarde, a base d'acide amine tertiaire, de nitrile d'acide amine tertiaire et de sels amines d'acide amine tertiaire
CA337,170A CA1089868A (fr)	1976-08-26	1979-10-09	Acides amines tertiaires, nitriles amines tertiaires et sels amines d'acides amines tertiaires formant des catalyseurs a effet retarde

Publications (1)

Publication Number	Publication Date
CA1089868A true CA1089868A (fr)	1980-11-18

Family

ID=27426010

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA337,170A Expired CA1089868A (fr)	1976-08-26	1979-10-09	Acides amines tertiaires, nitriles amines tertiaires et sels amines d'acides amines tertiaires formant des catalyseurs a effet retarde

Country Status (1)

Country	Link
CA (1)	CA1089868A (fr)

1979
- 1979-10-09 CA CA337,170A patent/CA1089868A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-11-18	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 19971118

Publication	Publication Date	Title
US4115634A (en)	1978-09-19	Amine salts of amino acids as delayed action catalysts
US4040992A (en)	1977-08-09	Catalysis of organic isocyanate reactions
US4101470A (en)	1978-07-18	Urethane catalysts
US3620984A (en)	1971-11-16	Polyurethane catalysts
US4094827A (en)	1978-06-13	Substituted ureas as polyurethane catalysts
US4049591A (en)	1977-09-20	Foams and elastomers prepared in the presence of high tertiary amine content polyurethane catalysts
US4282330A (en)	1981-08-04	Energy management polyether polyurethane foam
US4232152A (en)	1980-11-04	Amine salts of tertiary amino acids
KR20100034009A (ko)	2010-03-31	폴리우레탄 제조를 위한 수 안정성 촉매
KR100362550B1 (ko)	2002-11-30	폴리우레탄 가요성 발포체의 치수 안정성을 개선시키기위한 약 브뢴스테드산 유도체
CN1032216C (zh)	1996-07-03	生产聚氨酯泡沫塑料的方法
US4086213A (en)	1978-04-25	Tertiary amino acid and tertiary amino acid-nitrile delayed action catalyst compositions
KR101319112B1 (ko)	2013-10-17	신규한 지르코늄 화합물 촉매 및 폴리우레탄 제조에서의그의 용도
CA1083552A (fr)	1980-08-12	Catalyseurs a effet retarde, a base d'acide amine tertiaire, de nitrile d'acide amine tertiaire et de sels amines d'acide amine tertiaire
US20100311937A1 (en)	2010-12-09	Method and catalyst for the manufacture of a polyurethane
US4101466A (en)	1978-07-18	Bis (dimethylaminopropyl)-amine derivatives as polyurethane catalysts
US4390640A (en)	1983-06-28	Process for the production of optionally-foamed polyurethanes
US4204062A (en)	1980-05-20	Amine salts of tertiary amino acids
JPH038370B2 (fr)	1991-02-05
EP0318242A2 (fr)	1989-05-31	Polyols polymériques à haute teneur en solides
US4134994A (en)	1979-01-16	Amine salts of tertiary amino acids
CA1089868A (fr)	1980-11-18	Acides amines tertiaires, nitriles amines tertiaires et sels amines d'acides amines tertiaires formant des catalyseurs a effet retarde
EP0278436A2 (fr)	1988-08-17	Mélange-maître à base de polyol contenant une polyurée et contenant de catalyseurs pour des mousses de polyuréthane éliminant le changement de la réactivité
US4360670A (en)	1982-11-23	Amino and amido dialkyl tin carboxylates
US4223139A (en)	1980-09-16	Amine salts of tertiary amino acids