WO2008157153A1 - Reactive amine catalysts for polyurethane foam - Google Patents
Reactive amine catalysts for polyurethane foam Download PDFInfo
- Publication number
- WO2008157153A1 WO2008157153A1 PCT/US2008/066490 US2008066490W WO2008157153A1 WO 2008157153 A1 WO2008157153 A1 WO 2008157153A1 US 2008066490 W US2008066490 W US 2008066490W WO 2008157153 A1 WO2008157153 A1 WO 2008157153A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polyurethane
- foam
- catalysts
- carbons
- formula
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title abstract description 92
- 150000001412 amines Chemical class 0.000 title description 21
- 229920005830 Polyurethane Foam Polymers 0.000 title description 12
- 239000011496 polyurethane foam Substances 0.000 title description 12
- 229920002635 polyurethane Polymers 0.000 claims abstract description 44
- 239000004814 polyurethane Substances 0.000 claims abstract description 44
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 33
- -1 alkylene alcohol Chemical group 0.000 claims abstract description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- SCRPVVLMUUQILK-UHFFFAOYSA-N 3-[2-(dimethylamino)ethoxy]propan-1-amine Chemical compound CN(C)CCOCCCN SCRPVVLMUUQILK-UHFFFAOYSA-N 0.000 claims abstract description 6
- BPOJHKFBHRYIHZ-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n-methylethanamine Chemical compound CNCCOCCN(C)C BPOJHKFBHRYIHZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000006260 foam Substances 0.000 claims description 75
- 229920005862 polyol Polymers 0.000 claims description 41
- 150000003077 polyols Chemical class 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 29
- 230000008569 process Effects 0.000 claims description 19
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 15
- 229920000570 polyether Polymers 0.000 claims description 15
- 229920001228 polyisocyanate Polymers 0.000 claims description 14
- 239000005056 polyisocyanate Substances 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 7
- UOQYWMZLTNEIFI-UHFFFAOYSA-N 2-[3-aminopropyl(methyl)amino]ethanol Chemical compound OCCN(C)CCCN UOQYWMZLTNEIFI-UHFFFAOYSA-N 0.000 claims description 5
- 229920005906 polyester polyol Polymers 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 3
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 27
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- 239000012948 isocyanate Substances 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- 239000004604 Blowing Agent Substances 0.000 description 13
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- 150000002513 isocyanates Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 8
- 229920006389 polyphenyl polymer Polymers 0.000 description 7
- 150000003512 tertiary amines Chemical class 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 description 6
- 239000001569 carbon dioxide Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000007664 blowing Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 239000004872 foam stabilizing agent Substances 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000013518 molded foam Substances 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 239000012974 tin catalyst Substances 0.000 description 3
- 150000003606 tin compounds Chemical class 0.000 description 3
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 3
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920002396 Polyurea Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 229920013701 VORANOL™ Polymers 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 159000000032 aromatic acids Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 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 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- DTZHXCBUWSTOPO-UHFFFAOYSA-N 1-isocyanato-4-[(4-isocyanato-3-methylphenyl)methyl]-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(CC=2C=C(C)C(N=C=O)=CC=2)=C1 DTZHXCBUWSTOPO-UHFFFAOYSA-N 0.000 description 1
- AXFVIWBTKYFOCY-UHFFFAOYSA-N 1-n,1-n,3-n,3-n-tetramethylbutane-1,3-diamine Chemical compound CN(C)C(C)CCN(C)C AXFVIWBTKYFOCY-UHFFFAOYSA-N 0.000 description 1
- NCUPDIHWMQEDPR-UHFFFAOYSA-N 2-[2-[2-(dimethylamino)ethoxy]ethyl-methylamino]ethanol Chemical compound CN(C)CCOCCN(C)CCO NCUPDIHWMQEDPR-UHFFFAOYSA-N 0.000 description 1
- QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical compound C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-UHFFFAOYSA-N 0.000 description 1
- AWGBKZRMLNVLAF-UHFFFAOYSA-N 3,5-dibromo-n,2-dihydroxybenzamide Chemical compound ONC(=O)C1=CC(Br)=CC(Br)=C1O AWGBKZRMLNVLAF-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
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- 0 CCC(C)(CC(C)(CC)OC(C)(CC)CC(C)(CC)N(*)I)N(*)* Chemical compound CCC(C)(CC(C)(CC)OC(C)(CC)CC(C)(CC)N(*)I)N(*)* 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical group NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 206010019099 Halo vision Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241001425800 Pipa Species 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 229920006311 Urethane elastomer Polymers 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- KIBKSNLNGHPFTB-UHFFFAOYSA-L [acetyloxy(diethyl)stannyl] acetate Chemical compound CC([O-])=O.CC([O-])=O.CC[Sn+2]CC KIBKSNLNGHPFTB-UHFFFAOYSA-L 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
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- 125000005442 diisocyanate group Chemical group 0.000 description 1
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 1
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- 239000006185 dispersion Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- RJLZSKYNYLYCNY-UHFFFAOYSA-N ethyl carbamate;isocyanic acid Chemical compound N=C=O.CCOC(N)=O RJLZSKYNYLYCNY-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
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- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
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- 239000003999 initiator Substances 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- COPLXRFZXQINJM-UHFFFAOYSA-N isocyanic acid;hydrate Chemical compound O.N=C=O COPLXRFZXQINJM-UHFFFAOYSA-N 0.000 description 1
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- PGYPOBZJRVSMDS-UHFFFAOYSA-N loperamide hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)N(C)C)CCN(CC1)CCC1(O)C1=CC=C(Cl)C=C1 PGYPOBZJRVSMDS-UHFFFAOYSA-N 0.000 description 1
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- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
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Classifications
-
- 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
- C08G18/1833—Catalysts containing secondary or tertiary amines or salts thereof having ether, acetal, or orthoester groups
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4072—Mixtures of compounds of group C08G18/63 with other macromolecular compounds
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0008—Foam properties flexible
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0041—Foam properties having specified density
- C08G2110/005—< 50kg/m3
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0083—Foam properties prepared using water as the sole blowing agent
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2008266219A AU2008266219B2 (en) | 2007-06-19 | 2008-06-11 | Reactive amine catalysts for polyurethane foam |
JP2010513332A JP2010530469A (en) | 2007-06-19 | 2008-06-11 | Reactive amine catalysts for polyurethane |
US12/663,882 US8563676B2 (en) | 2007-06-19 | 2008-06-11 | Reactive amine catalysts for polyurethane foam |
CA2689510A CA2689510C (en) | 2007-06-19 | 2008-06-11 | Reactive amine catalysts for polyurethane foam |
CN2008800209503A CN101743264B (en) | 2007-06-19 | 2008-06-11 | Reactive amine catalysts for polyurethane foam |
EP08770649.5A EP2162480A4 (en) | 2007-06-19 | 2008-06-11 | Reactive amine catalysts for polyurethane foam |
MX2009013796A MX2009013796A (en) | 2007-06-19 | 2008-06-11 | Reactive amine catalysts for polyurethane foam. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US93626007P | 2007-06-19 | 2007-06-19 | |
US60/936,260 | 2007-06-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2008157153A1 true WO2008157153A1 (en) | 2008-12-24 |
Family
ID=40156593
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2008/066490 WO2008157153A1 (en) | 2007-06-19 | 2008-06-11 | Reactive amine catalysts for polyurethane foam |
Country Status (8)
Country | Link |
---|---|
US (1) | US8563676B2 (en) |
EP (1) | EP2162480A4 (en) |
JP (1) | JP2010530469A (en) |
CN (1) | CN101743264B (en) |
AU (1) | AU2008266219B2 (en) |
CA (1) | CA2689510C (en) |
MX (1) | MX2009013796A (en) |
WO (1) | WO2008157153A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2257592A2 (en) * | 2008-03-20 | 2010-12-08 | Huntsman Petrochemical LLC | Reduction of aldehydes in amines |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2817783C (en) * | 2010-11-29 | 2018-10-02 | Huntsman Corporation Hungary ZRt | Blowing catalyst |
DE102014215388A1 (en) * | 2014-08-05 | 2016-02-11 | Evonik Degussa Gmbh | Nitrogen containing compounds suitable for use in the production of polyurethanes |
KR101655563B1 (en) * | 2014-11-06 | 2016-09-07 | 주식회사 엘지화학 | Pouch case for secondary battery and pouch-type secondary battery comprising the same |
US10836856B2 (en) | 2015-01-05 | 2020-11-17 | Rhodia Operations | Amine-imino dialcohol neutralizing agents for low volatile compound aqueous organic coating compositions and methods for using same |
CN110317311A (en) * | 2018-03-28 | 2019-10-11 | 科思创德国股份有限公司 | The hard polyurethane foams of low smell |
WO2024020776A1 (en) | 2022-07-26 | 2024-02-01 | Dow Global Technologies Llc | Low odor silicone polyether type surfactants and their use in polyurethane compositions |
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US2683730A (en) | 1951-01-17 | 1954-07-13 | Goodyear Tire & Rubber | Polyisocyanates and mixtures thereof |
US2950263A (en) | 1957-05-10 | 1960-08-23 | Ici Ltd | Preparation of foamed castor oil citrate-organic polyisocyanate reaction products |
US3012008A (en) | 1957-03-29 | 1961-12-05 | Ici Ltd | Polyisocyanate compositions |
US3072082A (en) | 1960-05-19 | 1963-01-08 | Conrad Erich Henry | Schiffli type embroidery machine |
US3194773A (en) | 1957-09-25 | 1965-07-13 | Union Carbide Corp | Process of making polyurethane foams |
US3297597A (en) | 1963-06-17 | 1967-01-10 | Jefferson Chem Co Inc | Production of rigid polyurethane foam |
US3330782A (en) | 1963-11-12 | 1967-07-11 | Union Carbide Corp | Beta-(n, n-dimethylamino)alkyl ethers as catalysts for isocyanate reactions |
US3344162A (en) | 1964-01-02 | 1967-09-26 | Jefferson Chem Co Inc | Preparation of aromatic polyisocyanates |
US3362979A (en) | 1964-01-02 | 1968-01-09 | Jefferson Chem Co Inc | Mixtures of methylene-bridged polyphenyl polyisocyanates |
US4101470A (en) | 1976-11-11 | 1978-07-18 | Texaco Development Corp. | Urethane catalysts |
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US4433170A (en) | 1981-07-20 | 1984-02-21 | Texaco Inc. | Novel bis(aminoethyl)ether derivatives useful as polyurethane catalysts |
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US6759447B1 (en) * | 2003-01-06 | 2004-07-06 | Air Products And Chemicals, Inc. | Physical properties of polyurethane foams using tertiary amino alkyl amide catalysts |
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-
2008
- 2008-06-11 US US12/663,882 patent/US8563676B2/en active Active
- 2008-06-11 MX MX2009013796A patent/MX2009013796A/en active IP Right Grant
- 2008-06-11 CA CA2689510A patent/CA2689510C/en not_active Expired - Fee Related
- 2008-06-11 JP JP2010513332A patent/JP2010530469A/en not_active Ceased
- 2008-06-11 WO PCT/US2008/066490 patent/WO2008157153A1/en active Application Filing
- 2008-06-11 AU AU2008266219A patent/AU2008266219B2/en not_active Ceased
- 2008-06-11 EP EP08770649.5A patent/EP2162480A4/en not_active Withdrawn
- 2008-06-11 CN CN2008800209503A patent/CN101743264B/en active Active
Patent Citations (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2683730A (en) | 1951-01-17 | 1954-07-13 | Goodyear Tire & Rubber | Polyisocyanates and mixtures thereof |
US3012008A (en) | 1957-03-29 | 1961-12-05 | Ici Ltd | Polyisocyanate compositions |
US2950263A (en) | 1957-05-10 | 1960-08-23 | Ici Ltd | Preparation of foamed castor oil citrate-organic polyisocyanate reaction products |
US3194773A (en) | 1957-09-25 | 1965-07-13 | Union Carbide Corp | Process of making polyurethane foams |
US3072082A (en) | 1960-05-19 | 1963-01-08 | Conrad Erich Henry | Schiffli type embroidery machine |
US3297597A (en) | 1963-06-17 | 1967-01-10 | Jefferson Chem Co Inc | Production of rigid polyurethane foam |
US3330782A (en) | 1963-11-12 | 1967-07-11 | Union Carbide Corp | Beta-(n, n-dimethylamino)alkyl ethers as catalysts for isocyanate reactions |
US3344162A (en) | 1964-01-02 | 1967-09-26 | Jefferson Chem Co Inc | Preparation of aromatic polyisocyanates |
US3362979A (en) | 1964-01-02 | 1968-01-09 | Jefferson Chem Co Inc | Mixtures of methylene-bridged polyphenyl polyisocyanates |
US4101470A (en) | 1976-11-11 | 1978-07-18 | Texaco Development Corp. | Urethane catalysts |
US4338408A (en) | 1981-07-20 | 1982-07-06 | Texaco Inc. | Polyurethanes using bis(aminoethyl)ether derivatives as catalysts |
US4433170A (en) | 1981-07-20 | 1984-02-21 | Texaco Inc. | Novel bis(aminoethyl)ether derivatives useful as polyurethane catalysts |
US4940818A (en) * | 1987-06-30 | 1990-07-10 | Hoechst Aktiengesellschaft | Process on the preparation of 2,2'-oxybis(N,N-dimethyl-ethanamine) |
US5824711A (en) * | 1997-05-05 | 1998-10-20 | Air Products And Chemicals, Inc. | N,N,N'-trimethylbis (Aminoethyl) ether substituted urea compostions for the production of polyurethanes |
US6759447B1 (en) * | 2003-01-06 | 2004-07-06 | Air Products And Chemicals, Inc. | Physical properties of polyurethane foams using tertiary amino alkyl amide catalysts |
Non-Patent Citations (2)
Title |
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EVALUATION OF SOME POLYOLS IN ONE-SHOT RESILIENT FOAMS, 22 March 1960 (1960-03-22) |
See also references of EP2162480A4 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2257592A2 (en) * | 2008-03-20 | 2010-12-08 | Huntsman Petrochemical LLC | Reduction of aldehydes in amines |
EP2257592A4 (en) * | 2008-03-20 | 2013-06-05 | Huntsman Petrochemical Llc | Reduction of aldehydes in amines |
Also Published As
Publication number | Publication date |
---|---|
CN101743264B (en) | 2013-08-21 |
CA2689510C (en) | 2015-04-21 |
US8563676B2 (en) | 2013-10-22 |
EP2162480A1 (en) | 2010-03-17 |
MX2009013796A (en) | 2010-04-22 |
CN101743264A (en) | 2010-06-16 |
CA2689510A1 (en) | 2008-12-24 |
AU2008266219A1 (en) | 2008-12-24 |
EP2162480A4 (en) | 2014-01-22 |
AU2008266219B2 (en) | 2013-05-23 |
JP2010530469A (en) | 2010-09-09 |
US20100179297A1 (en) | 2010-07-15 |
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