WO1996006874A1 - Mousse souple de polyurethanne de densite reduite produite a partir de diphenylisocyanate de methylene - Google Patents
Mousse souple de polyurethanne de densite reduite produite a partir de diphenylisocyanate de methylene Download PDFInfo
- Publication number
- WO1996006874A1 WO1996006874A1 PCT/US1995/010717 US9510717W WO9606874A1 WO 1996006874 A1 WO1996006874 A1 WO 1996006874A1 US 9510717 W US9510717 W US 9510717W WO 9606874 A1 WO9606874 A1 WO 9606874A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- weight
- polyahl
- content
- oxyethylene
- percent
- Prior art date
Links
- 229920005830 Polyurethane Foam Polymers 0.000 title claims abstract description 32
- 239000011496 polyurethane foam Substances 0.000 title claims abstract description 32
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical compound O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 125000006353 oxyethylene group Chemical group 0.000 claims abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000006057 Non-nutritive feed additive Substances 0.000 claims abstract description 22
- 229920000570 polyether Polymers 0.000 claims abstract description 16
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 13
- 150000003077 polyols Chemical class 0.000 claims description 44
- 229920005862 polyol Polymers 0.000 claims description 40
- 229920001228 polyisocyanate Polymers 0.000 claims description 23
- 239000005056 polyisocyanate Substances 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- -1 polyoxypropylene-oxyethylene Polymers 0.000 claims description 16
- 239000012948 isocyanate Substances 0.000 claims description 13
- 150000002513 isocyanates Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 claims description 2
- 239000006260 foam Substances 0.000 abstract description 23
- 238000002360 preparation method Methods 0.000 abstract description 8
- 230000000704 physical effect Effects 0.000 abstract description 6
- 238000007664 blowing Methods 0.000 abstract description 5
- 239000004604 Blowing Agent Substances 0.000 description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 239000003570 air Substances 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000012973 diazabicyclooctane Substances 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 150000003606 tin compounds Chemical class 0.000 description 3
- 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 3
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 2
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 229920013701 VORANOL™ Polymers 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000004872 foam stabilizing agent Substances 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 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
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
- 229940029284 trichlorofluoromethane Drugs 0.000 description 2
- HOVAGTYPODGVJG-UVSYOFPXSA-N (3s,5r)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol Chemical compound COC1OC(CO)[C@@H](O)C(O)[C@H]1O HOVAGTYPODGVJG-UVSYOFPXSA-N 0.000 description 1
- FRCHKSNAZZFGCA-UHFFFAOYSA-N 1,1-dichloro-1-fluoroethane Chemical compound CC(F)(Cl)Cl FRCHKSNAZZFGCA-UHFFFAOYSA-N 0.000 description 1
- BHNZEZWIUMJCGF-UHFFFAOYSA-N 1-chloro-1,1-difluoroethane Chemical compound CC(F)(F)Cl BHNZEZWIUMJCGF-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 1
- ATEBGNALLCMSGS-UHFFFAOYSA-N 2-chloro-1,1-difluoroethane Chemical compound FC(F)CCl ATEBGNALLCMSGS-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
- 229920013708 Dow VORANOL™ CP 1421 Polyol Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229930006000 Sucrose Natural products 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 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
- 239000000654 additive Substances 0.000 description 1
- MOVRNJGDXREIBM-UHFFFAOYSA-N aid-1 Chemical compound O=C1NC(=O)C(C)=CN1C1OC(COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)CO)C(O)C1 MOVRNJGDXREIBM-UHFFFAOYSA-N 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007373 indentation Methods 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical class [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- HOVAGTYPODGVJG-UHFFFAOYSA-N methyl beta-galactoside Natural products COC1OC(CO)C(O)C(O)C1O HOVAGTYPODGVJG-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy 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
- 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
- C08G2110/0041—Foam properties having specified density
- C08G2110/0058—≥50 and <150kg/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
Definitions
- This invention relates to the preparation of a water-blown, methylene diphenylisocyanate-based (MDI) polyurethane foam, and particularly a flexible, slabstock polyurethane foam.
- MDI methylene diphenylisocyanate-based
- Polyurethane foam manufacturers frequently desire, for economic reasons, to prepare foam having a lower density without detriment to competitive physical properties.
- An obvious means of attaining a lower density foam is to increase the amount of blowing agent o present during the manufacturing process when reacting a polyisocyanate with a polyether or polyester polyol.
- volatile organic compounds such as, for example, trichlorof luoromethane or methylene chloride have been employed as "physical" blowing agents when preparing flexible polyurethane foam.
- the use of many physical blowing agents has largely ceased 5 with only water being used in preference as a "chemical" blowing means. Water reacts with the polyisocyanate generating in situ carbon dioxide which then functions as the blowing agent.
- this invention relates to a process for preparing a flexible polyurethane foam which comprises reacting a polyisocyanate with a polyahl in the presence of a processing aid and water, wherein: a) the polyisocyanate comprises a methylene diphenylisocyanate, or a modified methylene diphenylisocyanate having an isocyanate content of at least 18 weight percent; b) the polyahl comprises at least one polyoxypropylene-oxyethylene polyol containing at least two hydroxyl groups, said polyahl having an average equivalent weight of from 1600 to 5000, an average oxyethylene content of at least 10 weight percent based on its total weight, and an average primary hydroxyl content of at least 55 percent of its total hydroxyl content; and c) the processing aid comprises at least one monohydroxyl polyether having an equivalent weight of from 600 to 5000 and an oxyethylene content of from 25 to 75 weight percent, and wherein the processing aid is present in an amount of from 1 to 20 parts
- this invention relates to a flexible polyurethane foam obtained according to the above-defined process.
- this invention relates to an isocyanate-reactive composition suitable for preparing a flexible polyurethane foam which contains a polyahl, a processing aid, and water wherein:
- the polyahl comprising a polyoxyalkylene polyol, has at least two isocyanate- -reactive hydrogen atoms/molecule, an average equivalent weight of from 1600 to 5000, an average oxyethylene content of at least 10 weight percent based on its total weight, and an average primary hydroxyl content of at least 55 percent of its total hydroxyl content;
- the processing aid comprising one or more monohydroxyl polyethers having an equivalent weight of from 600 to 5000 and an oxyethylene content of from 25 to 75 weight percent, is present in an amount of from 1 to 20 parts per 100 parts by weight of (a);
- MDI metal-based polyurethane foam
- a flexible slabstock polyurethane foam exhibiting attractive load bearing properties and a reduced density.
- reduced density it is understood that the foam has a lower density in comparison to foam obtained from conventional art processes using the same amounts of blowing agents providing the same blowing potential.
- the free rise density of such foam typically is from 15 to 60 kg/m 3 , and preferably from 20 to 45 kg/m 3 .
- the load bearing properties of the foam may be characterized by a modulus or "SAG" factor performance generally of 2.5 or higher, and frequently of 3.0 or higher.
- such polyurethane foam can be prepared by reacting a polyisocyanate with a polyahl in the presence of a processing aid and water, and optionally catalyst, surfactant, flame retardant and other additives well known to those skilled in the art of preparing polyurethane foam.
- a processing aid and water and optionally catalyst, surfactant, flame retardant and other additives well known to those skilled in the art of preparing polyurethane foam.
- catalyst, surfactant, flame retardant and other additives well known to those skilled in the art of preparing polyurethane foam.
- the polyisocyanate used in the present invention comprises a methylene diphenylisocyanate (MDI) or a urethane-modified adduct thereof having an isocyanate content of at least 18 weight percent.
- MDI methylene diphenylisocyanate
- urethane-modified adduct thereof having an isocyanate content of at least 18 weight percent.
- MDI includes the isomers 4,4'- and 2,4'-methylene diphenylisocyanate in a weight ratio of advantageously from 98:2 to 50: 50, preferably from 95:5 to 70:30, and more preferably from 90: 10 to 70:30. Such a ratio is desirable to provide optimum physical properties including the SAG factor of the resulting foam. While it is preferred to use a polyisocyanate that consists essentially of 4,4'- and 2,4'-MDI isomers, such MDI isomers may also be used in admixture with polymeric polymethylene polyphenylisocyanate. When present, the amount of polymeric polymethylene polyphenylisocyanate in the total polyisocyanate mixture will be less than 30, and preferably less than 15 percent based on parts by weight of total polyisocyanate present.
- the urethane-modified adduct of MDI is obtained by reacting MDI with a polyoxyalkylene diol or triol, present in a substoichiometric amount, to provide the resulting adduct with an isocyanate content advantageously of from 20, preferably from 25, more preferably from 28, and preferably to 31, more preferably to 30 weight percent.
- Suitable and preferred urethane-modified polyisocyanates are disclosed in U.S. Patent 5,114,989 and exemplified by, for example, the urethane-modified polyisocyanate designated as ISONATE Ml 00 available from The Dow Chemical Company.
- the polyisocyanate is present in an amount sufficient to provide an isocyanate reaction index of typically from 50 to 90, preferably from 65, more preferably from 70, and preferably up to 85.
- An isocyanate reaction index of 100 corresponds to one isocyanate group per isocyanate reactive hydrogen atom including those present from the polyahl, processing aid and water.
- the Polyahl comprises at least one polyoxypropylene-oxyethylene polyol containing two or more hydroxyl groups, and preferably comprises at least two different polyoxypropylene-oxyethylene polyols.
- the polyahl can additionally include a variety of compounds and substances containing isocyanate-reactive hydrogen atoms such as amines, thiols, carboxylic acids and polyester polyols.
- the polyahl is characterized by its average equivalent weight, average oxyethylene content and average primary hydroxyl content. In general, the polyahl has an average equivalent weight of from 1600 to 5000, preferably from 1650, more preferably from 1700, preferably to 4000, more preferably to 3000.
- the polyahl has an average oxyethylene content of at least 10, preferably from 12, and more preferably from 14, preferably to 50, more preferably to 40, and most preferably to 30 percent based on its total weight.
- the oxyethylene content of the polyahl is understood to provide a good compatibility with water as present in the process of the invention.
- the polyahl has an average primary hydroxyl content of at least 55, preferably at least 60, more preferably at least 65 percent; preferably to 90, and more preferably to 85 percent of its total hydroxyl content.
- the polyahl advantageously has an average functionality of at least 2, preferably from 2.25 to 6, and more preferably from 2.25 to 4, and yet more preferably to 3.5.
- the term "functionality" is intended to mean the average number of isocyanate-reactive hydrogen atoms/molecule.
- the polyahl comprises at least one polyoxypropylene-oxyethylene polyol.
- Such polyol can be defined by the above-mentioned equivalent weight, oxyethylene content and primary hydroxyl percentage.
- the polyahl comprises a mixture of (i) a first polyoxyalkylene-oxyethylene polyol and (ii) a second polyoxyalkylene-oxyethylene polyol.
- a mixture advantageously, based on total weight of polyol (i) and polyol (ii) present, contains polyol (i) in an amount of from 60 to 98, preferably from 70 to 98, more o pre erably from 80 to 98, and most preferably from 80 to 95 weight percent; and polyol (ii) in an amount of from 2 to 40, preferably from 2 to 30, more preferably from 2 to 20, and most preferably from 5 to 15 weight percent.
- polyol (i) is as described above but limited to an oxyethylene content of less than 50, preferably from 10 to 40 weight percent; and advantageously has a functionality of from 2 to 6, preferably from 2 to 4.
- Polyol (ii) is 5 distinguished from polyol (i) in that it has an oxyethylene content of more than 50, preferably at least 60, and preferably up to 100, more preferably up to 85 weight percent; and an equivalent weight of from 500 to 5000, preferably from 1000 to 3000.
- Polyol (ii) advantageously has a functionality of from 2 to 6, preferably from 2 to 4.
- Suitable polyoxyalkylene polyols which may constitute the polyahl include those 0 which can be obtained by reacting an initiator containing two or more active hydrogen atoms with alkylene oxides comprising ethylene oxide, preferably in combination with propylene oxide or butylene oxide.
- Typical initiators include water, alkylene glycols, glycerine, trimethylolpropane, pentaerythritol, methylglucoside, sorbitol, mannitol, and sucrose.
- initiators include organic amines such as ethylene 5 diamine and toluene diamine; alkanolamines such as mono- or diethanolamine or diisopropanolamine; and aromatic resins such as phenol/ ormaldehyde condensates and phenol/formaldehyde/alkanolamine condensates.
- Preferred initiators include water, alkylene glycols, glycerine, trimethylolpropane and pentaerythritol.
- the preparation procedures for the polyols suitable for use in the process of the invention are well known to those skilled in the art 0 and do not require further explanation.
- Exemplary of commercially available polyether polyols corresponding to the above-defined components include, for example, for polyol (i), products designated as VORANOL EP1900, VORANOL CP6008 and VORALUX HP700; and for polyol (ii), VORANOL CP1421, all sold by The Dow Chemical Company.
- the polyahl may urther contain a stably dispersed particulate polymer in an amount of from 2 to 20, preferably from 4 to 12 weight percent, based on the total weight of the polyahl including particulate polymer.
- Suitable particulate polymers include polyurea (PHD), polyisocyanate - polyamine adducts (PIPA) and particularly styrene/acrylonitrile (SAN) adducts.
- Polyoxyalkylene polyols containing the particulate polymer can be prepared by, for example, in situ polymerizing of styrene with acrylonitrile in a polyoxyalkylene polyol corresponding, for example, to the above-described polyol (i) or (ii).
- Exemplary of commercially available polyether polyols further comprising a stably dispersed particulate polymer and suitable for use as a polyahl component in the present invention include for example products designated as VORALUX HN 201 available from The Dow Chemical Company.
- the present invention requires the presence of a processing aid to assist in the manufacture of the foam and additionally to enhance the SAG performance of the resulting o foam.
- the processing aid is present in an amount of from 1 to 20, preferably from 5, more preferably from 7, and preferably up to 15, and more preferably up to 12.5 parts per 100 parts by total weight of the polyahl.
- the processing aid comprises one or more monohydroxyl polyether substances having an equivalent weight of from 600 to 5000, preferably from 1000 to 4000, and more preferably from 1500 to 3500.
- the monohydroxyl polyether has an 5 oxyethylene content of from 25 to 75, preferably from 30 to 60, and more preferably from 35 to 55 percent based on its total weight, the balance comprising oxypropylene or oxybutylene units.
- Commercially available substances suitable for use as processing aids of this invention include products sold by The Dow Chemical Company under the trademark of SYNALOX such as, for example, SYNALOX 25-50B and especially SYNALOX 25-300B. 0 The
- the blowing agent used in the present invention comprises water which reacts with polyisocyanate leading to the in situ production of carbon dioxide.
- the water is present in an amount of from 2 to 10, preferably from 2.5 to 8, more preferably to 6.5, and most preferably to 5.5 parts per 100 parts by weight of total polyahl.
- the blowing agent consists of water.
- the blowing capacity provided by water may be supplemented by physical blowing agents.
- Exemplary of such physical blowing agents include fluorocarbons and chlorofluorocarbons such as, for example, dichlorotrifluoroethane (R-123), dichlorofluoroethane (R-141a), chlorodifluoroethane 0 (R-142b), tetrafluoroethane (R-134a), and chlorodifluoromethane (R-22); hydrocarbons such as butane, pentane, cyclopentane, hexane and cyclohexane; and entrained gases such as air, argon and nitrogen.
- the blowing agent is present in an amount to confer to the resulting foam a free rise density as already mentioned.
- chain extending agents include, for example, glycerine and diethanolamine.
- Foam stabilizing agents include silicon surfactants, for example, siloxane-oxyalkylene copolymers such as products sold under the trademark TEGOSTAB by Th. Goldschmidt AG including B-41 13, B-4690 and B-8681 ; and products sold by Air Products including the product designated as DABCO DC 5258.
- Suitable catalysts which may be used to promote the formation of urethane groups include tertiary amines and organometallic compounds especially tin compounds.
- tertiary amine compounds include N,N-dimethylcyclohexylamine,
- N,N-dimethylbenzylamine, N,N-dimethylethanolamine, bis(dimethylaminoethyl)ether and 1 , 4-diazobicyclo[2,2,2]octane; of tin compounds include stannous octoate and dibutyltin dilaurate.
- Combinations of amine and/or tin compounds as catalyst may advantageously be present.
- antimony-, phosphorus- or nitrogen-containing substances including for example, melamine, tris(chloroethyl)phosphonate or preferably halogen-free phosphorus compounds including for example triethylphosphate.
- MDI - A ISONATE M100, a proprietary urethane-modified MDI composition with an NCO content of 29 weight percent, available from The Dow Chemical Company.
- Polyol 1 A glycerine-initiated polyoxypropylene-oxyethylene polyol of 2000 equivalent weight, with an oxyethylene content of 14.5 percent, and primary OH content of 80 percent.
- Polyol 2 A glycerine-initiated polyoxypropylene-oxyethylene polyol of 1600 equivalent weight, with an oxyethylene content of 17 percent, and primary OH content of 85 percent, and further containing 21 weight percent of a particulate styrene/acrylonitrile polymer
- Polyol 3 A glycerine-initiated polyoxypropylene-oxyethylene polyol of 1670 equivalent weight with an oxyethylene content of 75 percent, and primary OH content of 50 percent.
- Processing Aid - 1 SYNALOX 25-300B a proprietary monohydroxyl polyether, available from The Dow Chemical Company, and understood to have a molecular weight of 3000 and an oxyethylene content of 50 percent.
- Catalyst 1 DABCO 33LV, an amine-based proprietary urethane-promoting catalyst available from Air Products.
- Catalyst 2 NIAX A-1, an amine-based proprietary urethane-promoting catalyst available from OSi Specialities.
- Catalyst 3 Stannous Octoate.
- Surfactant 1 TEGOSTAB B 8681, a silicone-based proprietary surfactant available from Th Goldschmidt AG.
- Surfactant 2 DABCO DC 5258, a silicone-based proprietary surfactant available from Air Products.
- Flexible, slabstock, polyurethane foam is prepared, according to the formulation given in Table I using a high pressure dispenser unit operating at 2900 rpm, with all component streams at 20 C C, and with a polyahl output of 25 kg/min. Properties of the resulting foam is reported in Table I.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
L'invention concerne la production de mousse de polyuréthanne, à base de diphénylisocyanate de méthylène, expansée à l'eau, notamment de mousse souple de polyuréthanne en bloc. Cette mousse est produite au moyen d'un auxiliaire de transformation comprenant au moins un polyéther de monohydroxyle présentant un poids équivalent compris entre 600 et 5000, ainsi qu'une teneur en oxyéthylène comprise entre 25 et 75 % en poids. Cet auxiliaire de transformation autorise une utilisation plus efficace de l'eau en tant qu'agent d'expansion et permet d'obtenir une mousse de densité réduite présentant des propriétés physiques intéressantes.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU34131/95A AU3413195A (en) | 1994-08-26 | 1995-08-23 | Reduced density flexible polyurethane foam from methylene diphenylisocyanate |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US29663294A | 1994-08-26 | 1994-08-26 | |
US08/296,632 | 1994-08-26 |
Publications (1)
Publication Number | Publication Date |
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WO1996006874A1 true WO1996006874A1 (fr) | 1996-03-07 |
Family
ID=23142852
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1995/010717 WO1996006874A1 (fr) | 1994-08-26 | 1995-08-23 | Mousse souple de polyurethanne de densite reduite produite a partir de diphenylisocyanate de methylene |
Country Status (2)
Country | Link |
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AU (1) | AU3413195A (fr) |
WO (1) | WO1996006874A1 (fr) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004020496A1 (fr) * | 2002-08-27 | 2004-03-11 | Shell Internationale Research Maatschappij B.V. | Combinaison de polyol |
US6914117B2 (en) | 2001-05-21 | 2005-07-05 | Huntsman International Llc | Elastomeric polyurethane material |
US6946497B2 (en) | 2001-04-27 | 2005-09-20 | Huntsman International Llc | Process for making visco-elastic foam |
US8901187B1 (en) | 2008-12-19 | 2014-12-02 | Hickory Springs Manufacturing Company | High resilience flexible polyurethane foam using MDI |
US8906975B1 (en) | 2009-02-09 | 2014-12-09 | Hickory Springs Manufacturing Company | Conventional flexible polyurethane foam using MDI |
US9255174B2 (en) | 2010-09-29 | 2016-02-09 | Dow Global Technologies Llc | Use of poly(butylene oxide) polyol to improve durability of MDI-polyurethane foams |
WO2017006357A1 (fr) | 2015-07-06 | 2017-01-12 | Dow Global Technologies Llc | Prépolymères de polyuréthane |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1487458A (fr) * | 1966-05-26 | 1967-07-07 | Naphtachimie Sa | Mousses de polyuréthane |
FR2268036A1 (en) * | 1974-04-19 | 1975-11-14 | Naphtachimie Sa | Polyurethane soft foams - obtd. from particular polyether polyols, polyisocyantes and crosslinking agents |
WO1994004586A1 (fr) * | 1992-08-14 | 1994-03-03 | Dow Europe S.A. | Mousses de polyurethane flexibles, moulees, durcies a chaud et a faible resistance mecanique |
-
1995
- 1995-08-23 WO PCT/US1995/010717 patent/WO1996006874A1/fr active Application Filing
- 1995-08-23 AU AU34131/95A patent/AU3413195A/en not_active Abandoned
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1487458A (fr) * | 1966-05-26 | 1967-07-07 | Naphtachimie Sa | Mousses de polyuréthane |
FR2268036A1 (en) * | 1974-04-19 | 1975-11-14 | Naphtachimie Sa | Polyurethane soft foams - obtd. from particular polyether polyols, polyisocyantes and crosslinking agents |
WO1994004586A1 (fr) * | 1992-08-14 | 1994-03-03 | Dow Europe S.A. | Mousses de polyurethane flexibles, moulees, durcies a chaud et a faible resistance mecanique |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6946497B2 (en) | 2001-04-27 | 2005-09-20 | Huntsman International Llc | Process for making visco-elastic foam |
US6914117B2 (en) | 2001-05-21 | 2005-07-05 | Huntsman International Llc | Elastomeric polyurethane material |
WO2004020496A1 (fr) * | 2002-08-27 | 2004-03-11 | Shell Internationale Research Maatschappij B.V. | Combinaison de polyol |
US8901187B1 (en) | 2008-12-19 | 2014-12-02 | Hickory Springs Manufacturing Company | High resilience flexible polyurethane foam using MDI |
US8906975B1 (en) | 2009-02-09 | 2014-12-09 | Hickory Springs Manufacturing Company | Conventional flexible polyurethane foam using MDI |
US9255174B2 (en) | 2010-09-29 | 2016-02-09 | Dow Global Technologies Llc | Use of poly(butylene oxide) polyol to improve durability of MDI-polyurethane foams |
WO2017006357A1 (fr) | 2015-07-06 | 2017-01-12 | Dow Global Technologies Llc | Prépolymères de polyuréthane |
Also Published As
Publication number | Publication date |
---|---|
AU3413195A (en) | 1996-03-22 |
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