CA2295639C - Improved water blown polyurethane soling systems - Google Patents
Improved water blown polyurethane soling systems Download PDFInfo
- Publication number
- CA2295639C CA2295639C CA002295639A CA2295639A CA2295639C CA 2295639 C CA2295639 C CA 2295639C CA 002295639 A CA002295639 A CA 002295639A CA 2295639 A CA2295639 A CA 2295639A CA 2295639 C CA2295639 C CA 2295639C
- Authority
- CA
- Canada
- Prior art keywords
- weight
- molded article
- diphenylmethane diisocyanate
- allophanate
- isocyanate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 23
- 239000004814 polyurethane Substances 0.000 title description 13
- 229920002635 polyurethane Polymers 0.000 title description 13
- 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 claims abstract description 60
- 239000012948 isocyanate Substances 0.000 claims abstract description 59
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 58
- 239000007788 liquid Substances 0.000 claims abstract description 23
- 239000004604 Blowing Agent Substances 0.000 claims abstract description 21
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 10
- 229920005830 Polyurethane Foam Polymers 0.000 claims abstract description 4
- 239000011496 polyurethane foam Substances 0.000 claims abstract description 4
- 230000001413 cellular effect Effects 0.000 claims abstract description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 53
- 229920005862 polyol Polymers 0.000 claims description 52
- 150000003077 polyols Chemical class 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 47
- 229920000570 polyether Polymers 0.000 claims description 39
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 35
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 26
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 21
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 19
- 150000002894 organic compounds Chemical class 0.000 claims description 11
- 239000007858 starting material Substances 0.000 claims description 11
- 239000006185 dispersion Substances 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 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 5
- 229920002396 Polyurea Polymers 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 4
- 229920000578 graft copolymer Polymers 0.000 claims 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 claims 1
- 229920000638 styrene acrylonitrile Polymers 0.000 claims 1
- 239000006260 foam Substances 0.000 abstract description 35
- 238000000034 method Methods 0.000 abstract description 29
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- -1 polyoxyethylene Polymers 0.000 description 38
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 27
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 17
- 238000012360 testing method Methods 0.000 description 15
- 238000009472 formulation Methods 0.000 description 12
- 229920001228 polyisocyanate Polymers 0.000 description 12
- 239000005056 polyisocyanate Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 11
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
- 238000005299 abrasion Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- 150000002009 diols Chemical class 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
- 150000003512 tertiary amines Chemical class 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 4
- 150000001718 carbodiimides Chemical class 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000002524 organometallic group Chemical group 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 150000001414 amino alcohols Chemical class 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 239000004872 foam stabilizing agent Substances 0.000 description 3
- 238000013038 hand mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- AWTOFSDLNREIFS-UHFFFAOYSA-N 1,1,2,2,3-pentafluoropropane Chemical compound FCC(F)(F)C(F)F AWTOFSDLNREIFS-UHFFFAOYSA-N 0.000 description 2
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 2
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 2
- ZRWNRAJCPNLYAK-UHFFFAOYSA-N 4-bromobenzamide Chemical compound NC(=O)C1=CC=C(Br)C=C1 ZRWNRAJCPNLYAK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 206010040925 Skin striae Diseases 0.000 description 2
- 208000031439 Striae Distensae Diseases 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 2
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- FYIRUPZTYPILDH-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoropropane Chemical compound FC(F)C(F)C(F)(F)F FYIRUPZTYPILDH-UHFFFAOYSA-N 0.000 description 1
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- OWRNLGZKEZSHGO-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-(2-hydroxypropoxy)propoxy]propoxy]propoxy]propoxy]propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)COC(C)COC(C)COC(C)COC(C)CO OWRNLGZKEZSHGO-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
-
- 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
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/7806—Nitrogen containing -N-C=0 groups
- C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
- C08G18/7837—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing allophanate 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
- C08G18/08—Processes
- C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
- C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
- C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
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- C08G18/40—High-molecular-weight compounds
- C08G18/409—Dispersions of polymers of C08G in organic compounds having active hydrogen
-
- 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
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- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
-
- 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
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/48—Polyethers
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- C08G18/4845—Polyethers containing oxyethylene units and other oxyalkylene units containing oxypropylene or higher oxyalkylene end 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
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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
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- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
-
- 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
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- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
- C08G18/725—Combination of polyisocyanates of C08G18/78 with other polyisocyanates
-
- 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
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- 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
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- 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
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/125—Water, e.g. hydrated salts
-
- 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
- C08G2110/0033—Foam properties having integral skins
-
- 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
- C08G2110/0066—≥ 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
-
- 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
- C08G2410/00—Soles
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S521/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S521/914—Polyurethane cellular product formed from a polyol which has been derived from at least two 1,2 epoxides as reactants
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Footwear And Its Accessory, Manufacturing Method And Apparatuses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/899,556 US5889068A (en) | 1997-07-24 | 1997-07-24 | Water blown polyurethane soling systems |
| US08/899,556 | 1997-07-24 | ||
| PCT/US1998/014536 WO1999005195A1 (en) | 1997-07-24 | 1998-07-14 | Improved water blown polyurethane soling systems |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2295639A1 CA2295639A1 (en) | 1999-02-04 |
| CA2295639C true CA2295639C (en) | 2007-09-18 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002295639A Expired - Fee Related CA2295639C (en) | 1997-07-24 | 1998-07-14 | Improved water blown polyurethane soling systems |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5889068A (enExample) |
| EP (1) | EP0998509B1 (enExample) |
| JP (1) | JP4198878B2 (enExample) |
| KR (1) | KR20010022144A (enExample) |
| CN (1) | CN1114641C (enExample) |
| AU (1) | AU8484198A (enExample) |
| BR (1) | BR9810786A (enExample) |
| CA (1) | CA2295639C (enExample) |
| DE (1) | DE69802287T2 (enExample) |
| ES (1) | ES2163285T3 (enExample) |
| IL (1) | IL133654A0 (enExample) |
| PL (1) | PL338185A1 (enExample) |
| WO (1) | WO1999005195A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1118501C (zh) * | 1997-12-26 | 2003-08-20 | 花王株式会社 | 用于鞋底的聚氨酯泡沫塑料 |
| EP0927738A3 (en) | 1997-12-30 | 2000-12-20 | Basf Corporation | Integral skin foams employing pentafluoropropane blowing agents |
| US6660782B1 (en) | 1998-04-22 | 2003-12-09 | Essex Specialty Products, Inc. | Rigid polyurethane foams and method to form said foams using low molecular weight diols and triols |
| KR100397668B1 (ko) * | 2000-10-24 | 2003-09-19 | 주식회사 세이빈엔지니어링 | 화장실 고체전달음 차단용 변기소음 방진시트 |
| DE10062410A1 (de) | 2000-12-14 | 2002-06-20 | Bayer Ag | Verfahren zur Herstellung von Polyurethanelastomeren mit hohem Wärmestandverhalten |
| JP4159315B2 (ja) * | 2001-09-20 | 2008-10-01 | セントラル硝子株式会社 | 硬質ポリウレタンフォームまたはポリイソシアヌレートフォームの調製用のプレミックス、該フォームの製造方法および該フォーム |
| US6887399B2 (en) * | 2002-09-09 | 2005-05-03 | Bayer Materialscience Llp | Polymeric allophanates of diphenylmethane diisocyanate, prepolymers of these polymeric allophanates, and processes for the preparation of the polymeric allophanates and the prepolymers thereof |
| US20140194544A1 (en) * | 2004-04-29 | 2014-07-10 | Honeywell International Inc. | Foaming agents and compositions containing fluorine substituted olefins, and methods of foaming |
| US20040154718A1 (en) * | 2003-02-06 | 2004-08-12 | Doesburg Van I. | Polyurethane filled tire and method of making same |
| DE602004004561T2 (de) * | 2003-03-18 | 2007-11-15 | Tosoh Corp. | Katalysatorzusammensetzung für die Herstellung von Polyurethanharz und Verfahren zu ihrer Herstellung |
| US20180161076A1 (en) | 2003-10-27 | 2018-06-14 | Honeywell International Inc. | Foaming agents and compositions containing fluorine substituted olefins, and methods of foaming |
| KR100794133B1 (ko) | 2006-06-02 | 2008-01-10 | 에스케이씨 주식회사 | 탄성과 내구성이 우수한 난황변 연질 폴리우레탄 폼의제조방법 |
| KR100840997B1 (ko) | 2006-10-02 | 2008-06-24 | 에스케이씨 주식회사 | 폴리우레탄폼 제조용 폴리에테르폴리올의 제조방법 |
| JP5379964B2 (ja) * | 2006-10-11 | 2013-12-25 | エスケー化研株式会社 | 高分子化合物 |
| RU2487899C2 (ru) * | 2007-11-14 | 2013-07-20 | Басф Се | Пенополиуретаны с улучшенной усталостной прочностью при многократном изгибе |
| EP2385959B1 (de) * | 2009-01-12 | 2014-10-15 | Basf Se | Hochelastische polyurethanweichschaumstoffe |
| US10066047B2 (en) * | 2012-02-02 | 2018-09-04 | Covestro Llc | Polyurethane foams with decreased aldehyde emissions, a process for preparing these foams and a method for decreasing aldehyde in polyurethane foams |
| CN103756288B (zh) * | 2013-12-20 | 2016-10-12 | 苏州市万泰真空炉研究所有限公司 | 一种可生物降解的环保型硬质泡沫塑料复合物的制备方法 |
| US10081700B2 (en) * | 2015-05-05 | 2018-09-25 | Evonik Degussa Gmbh | Delayed action gelling catalyst compositions and methods for making polyurethane polymers |
| CN109535383B (zh) * | 2017-09-21 | 2022-07-15 | 科思创德国股份有限公司 | 一种二异氰酸酯组合物及其应用 |
| CN110627991B (zh) * | 2019-09-30 | 2021-09-24 | 长华化学科技股份有限公司 | 低密度高性能高回弹聚氨酯泡沫塑料及其制备方法和应用 |
| CN111234764B (zh) * | 2020-03-06 | 2021-02-02 | 杭州之江新材料有限公司 | 一种高粘接强度的聚氨酯组角胶及其制备方法 |
| CN116622050B (zh) * | 2023-07-21 | 2023-12-05 | 山东一诺威聚氨酯股份有限公司 | 低密度耐磨防滑聚氨酯鞋底树脂及其制备方法和应用 |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB994890A (en) * | 1961-12-18 | 1965-06-10 | Ici Ltd | New organic polyisocyanates and their manufacture |
| IT728734A (enExample) * | 1964-07-31 | 1900-01-01 | ||
| DE1618380C3 (de) * | 1967-03-08 | 1975-09-11 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung eines bei Raumtemperatur flüssigen Diphenylmethan-diisocyanatpräparates |
| US3836487A (en) * | 1968-09-23 | 1974-09-17 | Goodyear Tire & Rubber | High impact rigid self-skinned polyurethane foam and method |
| BE757939A (fr) * | 1969-10-24 | 1971-04-01 | Bayer Ag | Procede de preparation de matieres en mousses |
| JPS5533432B2 (enExample) * | 1971-12-08 | 1980-08-30 | ||
| DE2319648C2 (de) * | 1973-04-18 | 1985-08-14 | Bayer Ag, 5090 Leverkusen | Weitere Ausbildung des Verfahrens zur Herstellung von Schaumstoffen mit vorzüglichen Entformungseigenschaften |
| DE2363452C2 (de) * | 1973-12-20 | 1983-10-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Schaumstoffen |
| DE2513817C3 (de) * | 1975-03-27 | 1986-11-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Schaumstoff-Formkörpern kompakter Randzone und zelligem Kern |
| US4020001A (en) * | 1975-03-31 | 1977-04-26 | The Goodyear Tire & Rubber Company | Diol curative for polyurethane |
| US4055548A (en) * | 1976-09-17 | 1977-10-25 | The Upjohn Company | Storage-stable liquid polyisocyanate composition |
| US4118411A (en) * | 1977-02-09 | 1978-10-03 | Mobay Chemical Corporation | Low-temperature storage stable liquid diphenylmethane diisocyanates |
| US4115429A (en) * | 1977-03-18 | 1978-09-19 | Mobay Chemical Corporation | Low-temperature storage stable liquid diphenylmethane diisocyanates |
| DE2729990A1 (de) * | 1977-07-02 | 1979-01-18 | Bayer Ag | Verfahren zur herstellung von isocyanatgruppen aufweisenden allophanaten |
| DE2965737D1 (de) * | 1978-10-03 | 1983-07-28 | Ici Plc | Liquid polyisocyanate compositions |
| DE2914134A1 (de) * | 1979-04-07 | 1980-10-23 | Bayer Ag | Verfahren zur herstellung von polyurethan-schaumstoffen |
| US4477602A (en) * | 1983-07-25 | 1984-10-16 | Mobay Chemical Corporation | Novel system for the production of polyurethanes |
| US4490300A (en) * | 1983-09-30 | 1984-12-25 | Mobay Chemical Corporation | Liquid diphenylmethane diisocyanate compositions |
| US4490301A (en) * | 1983-09-30 | 1984-12-25 | Mobay Chemical Corporation | Liquid diphenylmethane diisocyanate compositions |
| US4546122A (en) * | 1984-08-06 | 1985-10-08 | Mobay Chemical Corporation | Flexible polyurethane foams |
| US4738991A (en) * | 1987-01-23 | 1988-04-19 | Basf Corporation | Storage stable polyisocyanates characterized by allophanate linkages |
| US4866103A (en) * | 1987-10-16 | 1989-09-12 | Ici Americas Inc. | Polyisocyanate compositions |
| US5166183A (en) * | 1991-04-16 | 1992-11-24 | Miles Inc. | Water-blown integral skin polyurethane foams |
| DE4122872A1 (de) * | 1991-07-11 | 1993-01-14 | Bayer Ag | Formschaumstoffe |
| US5332763A (en) * | 1992-07-10 | 1994-07-26 | Miles Inc. | Stable dispersions and their use in the preparation of polyurethane foams |
| DE19502198A1 (de) * | 1995-01-25 | 1996-08-01 | Bayer Ag | Verfahren zur Herstellung von Formkörpern |
| DE19519335A1 (de) * | 1995-05-26 | 1996-11-28 | Basf Ag | Verfahren zur Herstellung von Ester- und Urethangruppen enthaltenden Formkörpern, estergruppenhaltige Isocyanat-Semipräpolymere hierfür und ihre Verwendung |
| US5514723A (en) * | 1995-09-26 | 1996-05-07 | Bayer Corporation | Water-blown integral skin polyurethane foams and catalysts useful therein |
| US5618967A (en) * | 1995-10-30 | 1997-04-08 | Basf Corporation | Isocyanate composition |
| US5624966A (en) * | 1995-10-30 | 1997-04-29 | Basf Corporation | Process of making an integral skin polyurethane article |
| CA2207468A1 (en) * | 1996-07-15 | 1998-01-15 | Edmund J. Madaj | Water blown polyurethane integral skin foam having improved abrasion resistance |
| DE19649829A1 (de) * | 1996-12-02 | 1998-06-04 | Bayer Ag | Weichelastische Polyurethanschaumstoffe und ein Verfahren zu deren Herstellung |
| US5821275A (en) * | 1997-11-10 | 1998-10-13 | Bayer Corporation | Flexible foams and flexible molded foams based on liquid isocyanate-terminated allophanate-modified MDI prepolymer blends and processes for the production of these foams |
-
1997
- 1997-07-24 US US08/899,556 patent/US5889068A/en not_active Expired - Lifetime
-
1998
- 1998-07-14 CA CA002295639A patent/CA2295639C/en not_active Expired - Fee Related
- 1998-07-14 KR KR1020007000714A patent/KR20010022144A/ko not_active Ceased
- 1998-07-14 AU AU84841/98A patent/AU8484198A/en not_active Abandoned
- 1998-07-14 CN CN98807553A patent/CN1114641C/zh not_active Expired - Fee Related
- 1998-07-14 ES ES98935643T patent/ES2163285T3/es not_active Expired - Lifetime
- 1998-07-14 DE DE69802287T patent/DE69802287T2/de not_active Expired - Fee Related
- 1998-07-14 IL IL13365498A patent/IL133654A0/xx unknown
- 1998-07-14 PL PL98338185A patent/PL338185A1/xx unknown
- 1998-07-14 EP EP98935643A patent/EP0998509B1/en not_active Expired - Lifetime
- 1998-07-14 WO PCT/US1998/014536 patent/WO1999005195A1/en not_active Ceased
- 1998-07-14 BR BR9810786-0A patent/BR9810786A/pt not_active IP Right Cessation
- 1998-07-14 JP JP2000504183A patent/JP4198878B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| PL338185A1 (en) | 2000-10-09 |
| KR20010022144A (ko) | 2001-03-15 |
| ES2163285T3 (es) | 2002-01-16 |
| DE69802287T2 (de) | 2002-05-16 |
| AU8484198A (en) | 1999-02-16 |
| JP4198878B2 (ja) | 2008-12-17 |
| US5889068A (en) | 1999-03-30 |
| WO1999005195A1 (en) | 1999-02-04 |
| HK1034984A1 (en) | 2001-11-09 |
| CA2295639A1 (en) | 1999-02-04 |
| CN1114641C (zh) | 2003-07-16 |
| IL133654A0 (en) | 2001-04-30 |
| JP2003524661A (ja) | 2003-08-19 |
| BR9810786A (pt) | 2000-07-25 |
| DE69802287D1 (de) | 2001-12-06 |
| EP0998509A1 (en) | 2000-05-10 |
| CN1284092A (zh) | 2001-02-14 |
| EP0998509B1 (en) | 2001-10-31 |
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