SG192822A1 - Producing pu rigid foams materials - Google Patents
Producing pu rigid foams materials Download PDFInfo
- Publication number
- SG192822A1 SG192822A1 SG2013062484A SG2013062484A SG192822A1 SG 192822 A1 SG192822 A1 SG 192822A1 SG 2013062484 A SG2013062484 A SG 2013062484A SG 2013062484 A SG2013062484 A SG 2013062484A SG 192822 A1 SG192822 A1 SG 192822A1
- Authority
- SG
- Singapore
- Prior art keywords
- rigid foams
- polyurethane rigid
- producing polyurethane
- oxide
- polyether alcohol
- Prior art date
Links
- 239000006260 foam Substances 0.000 title claims abstract description 39
- 239000000463 material Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 49
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 239000004814 polyurethane Substances 0.000 claims abstract description 35
- 229920002635 polyurethane Polymers 0.000 claims abstract description 33
- 239000004604 Blowing Agent Substances 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 9
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 35
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 34
- 229920000570 polyether Polymers 0.000 claims description 34
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 32
- 125000002947 alkylene group Chemical group 0.000 claims description 31
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 27
- -1 amino- Chemical class 0.000 claims description 27
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 24
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 24
- 229920000877 Melamine resin Polymers 0.000 claims description 23
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 14
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 10
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 9
- 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 claims description 8
- 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 claims description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 8
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 8
- 239000000600 sorbitol Substances 0.000 claims description 8
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 6
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 150000004982 aromatic amines Chemical class 0.000 claims description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- 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 claims description 4
- 229930006000 Sucrose Natural products 0.000 claims description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 239000002666 chemical blowing agent Substances 0.000 claims description 4
- 239000005720 sucrose Substances 0.000 claims description 4
- 238000009435 building construction Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000003860 storage Methods 0.000 claims description 3
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 claims description 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 claims description 2
- 229940043276 diisopropanolamine Drugs 0.000 claims description 2
- 239000011810 insulating material Substances 0.000 claims description 2
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 229920005862 polyol Polymers 0.000 description 15
- 150000003077 polyols Chemical class 0.000 description 15
- 239000003999 initiator Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 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
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000010517 secondary reaction Methods 0.000 description 3
- 239000010959 steel Substances 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- 239000013543 active substance Substances 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000005844 autocatalytic reaction Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001924 cycloalkanes Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 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
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 2
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- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 description 1
- QXRRAZIZHCWBQY-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1(CN=C=O)CCCCC1 QXRRAZIZHCWBQY-UHFFFAOYSA-N 0.000 description 1
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 1
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- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- MASBWURJQFFLOO-UHFFFAOYSA-N ammeline Chemical compound NC1=NC(N)=NC(O)=N1 MASBWURJQFFLOO-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- 150000003946 cyclohexylamines Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical compound CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005903 polyol mixture Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000005436 troposphere Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
-
- 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
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5054—Polyethers having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- C08G18/5063—Polyethers having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing three nitrogen atoms in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—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
- C08G18/48—Polyethers
- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/482—Mixtures of polyethers containing at least one polyether containing 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
- C08G18/28—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
- C08G18/48—Polyethers
- C08G18/4829—Polyethers containing at least three hydroxy 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
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
-
- 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
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino 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
- C08G18/70—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
- 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
-
- 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
- C08G2101/00—Manufacture of cellular products
-
- 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
- C08G2110/0025—Foam properties rigid
-
- 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
15Producing PU rigid foams Abstract5 The present invention relates to a process for producing polyurethane (PU) rigid foams by reaction of polyisocyanates with compounds having two or more isocyanate-reactIve hydrogen atoms in the presence of blowing agents. No suitable figure
Description
Producing PU rigid foams !
The present invention relates to a process for producing polyurethane (PU) rigid foams by reaction of polyisocyanates with compounds having two or more isocyanate-reactive hydrogen atoms in the presence of blowing agents.
Polyurethane rigid foams are long known and are predominantly used for thermal insulation, for example in refrigerating appliances, hot water storage systems, district heating pipes or building construction, for example in sandwich elements. A comprehensive overview of the production and use of isocyanate-based rigid foams is given for example in Kunststoffi-Handbuch, volume 7, Polyurethanes, 1st edition 1966, edited by Dr. R. Vieweg and Dr. A. Hochtlen, and 2m edition 1983, edited by Dr. Giinter Oertel, and 3 edition 1993, edited by Dr. Glinter Oertel, Carl
Hanser Verlag, Munich, Vienna.
Isocyanate-based rigid foams are typically produced using polyols having high functionalities and relatively short chains in order that optimum crosslinking of foams may be ensured. The preferred polyether alcohols usually have a functionality of 4 to 8 and a hydroxyl number between 300 and 600 and more particularly between 400 and 500 mg KOH/g. It is known that polyols with a very high functionality and hydroxyl numbers between 300 and 600 have a very high viscosity, and so they cannot be used in formulations to be processed on customary manufacturing equipment. It is also known that polyols of this type are very polar and thus have poor solubility for hydrocarbons. To remedy this defect, the polyol component frequently includes polyether alcohols having functionalities between 2 and 4 and a hydroxy! number ranging from 250 to 450 mg KOH/g. WO2008/058863 describes a polyurethane rigid foam produced using a polyether alcohol based on TDA (tolylenediaming), Polyols of this type are notable for a relatively low functionality and cause late curing of the polyurethane system.
Hence even complicated cavities of the type occurring in refrigerating equipment in particular can be fully filled therewith. It is known that the flowability of polyol components based on high- functionality, polar polyols is not always satisfactory.
EP 1 138 709 discloses that rigid foams having good flowability are obtainable when compounds having two or more isocyanate-reactive hydrogen atoms comprise at least one polyether alcohol having a hydroxyl number of 100 to 250 mg KOH/g and obtained by addition of alkylene oxides onto H-functional starting substances having 2 to 4 active hydrogen atoms, more particularly glycols, trimethylolpropane, glycerol, pentaerythritol or TDA (tolylenediamine).
The foams obtained by the processes described still do not meet all technical requirements. 40
The problem addressed by the present invention is therefore that of providing a process for producing polyurethane rigid foams having optimum flow characteristics coupled with iow viscosity for the polyol component. In addition, high solubility of the generally apolar blowing agents in the system and a compatibility between the polyols used should be ensured. At the same time, a high compressive strength should be achieved to allow low densities to be established in the structural component.
Surprisingly, this problem is solved when melamine polyetherols are used as a component of the rigid foam formulation.
Melamine polyetherols are obtainable for example by ring-opening polymerization of alkylene oxides with melamine/co-initiator mixtures as described in DE 3 412 082 A1 for example.
The present invention thus provides a process for producing polyurethane rigid foams, which comprises (a) reacting at least one polyisocyanate by using (b) at least one blowing agent with (c) three or more different compounds each having two or more isocyanate-reactive hydrogen atoms, wherein (i) one of the three or more different compounds each having two or more isocyanate-reactive hydrogen atoms is a polyether alcohol component obtainable by reacting a mixture of melamine and at least one further hydroxyl- and/or amino-functional compound having a functionality ranging from 2 to 8 with at least one alkylene oxide, and (ii) a further one of the three or more different compounds each having two or more isocyanate-reactive hydrogen atoms is a polyether alcohol component having a hydroxyl number of 300 to 600 mg KOH/g coupled with an average functionality of 4 to 8, and (iii) the third one of the three or more different compounds each having two or more isocyanate-reactive hydrogen atoms is a polyether alcohol and/or polyester alcohol component having a hydroxyl number of 100 to 350 mg KOH/g coupled with an average functionality of 2 to 5 and preferably 2 to 4.
Hydroxyl number is measured according to German Standard Specification DIN 53240; average functionality relates to free OH groups.
The present invention further provides polyurethane rigid foams obtainable by the process of the present invention, and also the use of a polyurethane rigid foam obtainable by the process of the present invention as thermal insulating material in refrigerating appliances, hot water storage systems, district heating pipes or building construction.
In one embodiment of the process according to the present invention, the polyether alcohol component (i) is obtained without a catalyst.
In a further embodiment of the process according to the present invention, the polyether alcohol component (i) is obtainable by reacting a mixture of melamine and a further hydroxyl- and/or amino-functional compound in a mass ratio ranging from 3:1 to 1:3 and a mixture functionality in the range from 4 to 6, with at least one alkylene oxide. 40 Component (i) is obtained using as coinitiator compound reacted in the process with the alkylene oxide together with the melamine in the reaction mixture, at least one further hydroxyi- and/or amino-functional compound having a functionality of 2-8 and preferably of 2-6.
The hydroxyl-functional compound under (i) may be selected from the group ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,3-propanedial, 1,4-butanediot, neopentyiglycol, 1,5-pentanediol, 3-methyl-1,5-pentanediol, 1,6-hexanediol, 1,9-nonanediol, 2- methyl-1,8-octanediol, cyclohexanediol or dichlorohexanedimethanol, glycerol, trimethylolpropane, trimethylolethane, pentaerythritol, sucrose, sacarose, glucose, fructose, mannose, sorbitol, dipentaerythritol, tripentaerythritol, polyesters such as, for example, polyesters based on caprolactone or 1,4-butanediol and adipic acid, initiators based on renewable raw materials e.g., hydroxyl-containing fats such as, for example, castor oil or other hydroxyl-modified natural oils such as sunflower oil, soybean oil, rapeseed oi, palm oil, etc., and/or hydroxyl-containing fatty acid esters such as hydroxyalkyl stearate, hydroxyalkyl! oleate, hydroxyalkyl linolate, hydroxyalkyl linoleoate specifically methyl esters and ethyl esters of hydroxy fatty acids, lignin and/or salts thereof such as, for example, ligninsulfonate, polysaccharides, such as starch, cellulose, guar. + The amino-functional compound under (i) may be selected from the group ammonia, butylamine, aniline, methoxyaniline, cyclohexylamines, 2-ethylhexylamine, dimethylamine, diethylamine, ethylenediamine, N-methylanitine, N-ethylaniline, 1,3-diaminopropane, 3-{N,N- dimethylamino)propylamine, 2,3-tolylenediamine, 2,4-tolylenediamine, 2,6-tolylenediamine, phenylenediamine, or mixtures thereof. Ethanolarmine, isopropanoclamine, aminophenol, diethanolamine, N-methylmonoethanolamine, N-methyldiethanolamine, N-methylaminophenaol, triethanolamine, tris(hydroxymethyl)aminomethane, friisopropanolamine, N,N- dimethylethanolamine, monoethanotamine, diethanolamine, diethylenediamine.
The hydroxyl- or amino-functional compounds under (i) may each be used as pure substances or as mixiures.
Optionally, (i) may also utilize alkylene oxide addition products of the abovementioned initiator substances or addition products of melamine as coinitiators in the process. It is further conceivable for the reaction product of the above-described process itself to be used as a coinifiator in the reaction mixture together with the melamine.
In a further embodiment of the process according to the present invention, the polyether alcohol component (f) is obtainable by reacting a mixture of melamine and a further hydroxyl- and/or amino-functional compound selected from the group comprising glycerol, propylene glycol, ethylene glycol, dipropylene glycol, diethylene glycol, trimethylolpropane, sorbitol, urea, biuret, triethanolamine, diethanolamine, ethanolamine, trisopropanolamine, diisopropanolamine, isopropanoiamine, ethylenediamine (EDA), tolylenediamine (TDA) and methylenedianiline (MDA), with at least one alkylene oxide. 40
In a further embodiment of the process according to the present invention, the at least one alkylene oxide under (i} is selected from the group comprising propylene oxide, ethylene oxids,
1,2-butylene oxide and styrene oxide; preference is given to using propylene oxide or propylene oXide/ethylene oxide mixtures.
In a preferred embodiment of the process according fo the present invention, the polyether alcohol component (i) is obtainable by reacting a mixture of melamine and a further hydroxyl- and/or amino-functional compound selected from the group comprising glycerol, propylene glycol, ethylene glycol, dipropylene glycol, diethylene glycol, trimethyloipropane, sorbitol, triethanolamine, ethanolamine, tolylenediamine, with at least one alkylene oxide, wherein the alkylene oxide is selected from the group comprising propylene oxide and propylene oxide/ethylene oxide mixtures.
In a further embodiment of the process according to the present invention, the polyether alcohol component (i) is obtained in a temperature range between 120 and 180°C.
Instead of melamine (unsubstituted 2,4,6-triamino-1,3,5-triazine), other aminotriazines also come into consideration under (i), for example hydroxyl-, alkyl- or aryl-substituted aminofriazines, e.g., benzoguanamine, valeroguanaming, hexanoguanamine, lauroguanamine, stearoguanamine, acetoguanaming, caprinoguanamine or ammeline or mixtures thereof.
However, it is preferable to use unsubstituted 2,4,6-triamino-1,3,5-iriazine (also called melamine). The aminofriazine can be used as pure substance or as mixture with other aminotriazines.
In component (i}, the ratio of melamine to the coinitiator (i.e., to the at least one further hydroxyl- and/or amino-functional compound) in the initiator mixture Is generally in the range from 95:5 to 5:85 mass percent, preferably in the range from 30:70 to 70:30 mass percent and more preferably in the range from 40:60 to 60:40 mass percent.
The addition reaction of the alkylene oxide involved in obtaining component (i) can take place in the presence of basic alkylene oxide addition catalysts such as alkali metal hydroxides or alkaii metal alkoxides and also amines. In a mare advantageous and preferred embodiment, the addition reaction entirely takes place without the presence of alkylene oxide addition catalysts.
The alkylene oxide addition reaction involved in obtaining component (i) takes place at temperatures of 100°C to 200°C, preferably of 120° to 180°C, and more preferably of 140°C to 170°C. The reaction takes place in the pressure range between 0 and 20 bar and preferably between 0 and 10 bar.
The alkylene oxide for the reaction to obtain component (i) can be wholly or partly included in the initial charge together with the initiator mixture of melamine and at ieast one further hydroxyl- and/or amino-functional compound and wholly or partly added during the reaction. As 40 aresult, the process can be carried out in batch mode or in semibatch mode, the semibatch process being preferred. It is further possible to add the initiator mixture before or during the synthesis. A further possibility is to perform the entire manufacturing operation continuously, in which case the initiator mixture and the alkylene oxide and/or alkylene oxide mixture are added and some of the reaction product is continuously removed from the reaction batch.
After the reaction has ended, the reaction product, i.e., component (i), is freed of residual 5 monomer and of further volatile constituents by applying a vacuum. Optionally, a gas stream can be passed through the end product during the evacuation. Nitrogen and/or water vapor can be used as gas for the vacuum stripping. It is also conceivable to perform a sequential vacuum stripping operation by, for example, first stripping with water vapor and then with nitrogen.
After the reaction product, i.e., component (i), has been freed of residual monomer, it can optionally be neutralized by addition of acidic substances such as phosphoric acid, sulfuric acid, hydrochloric acid, nitric acid and/or CO. and subsequent filtration. This is necessary particularly when the addition reaction of the alkylene oxides takes place in the presence of alkali metal hydroxide or alkali metal alkoxide catalysts. In the case of autocatalytic reaction of the initiator compounds with alkylene oxides, this process step is not needed. As mentioned, the autocatalytic reaction with alkylene oxides is preferred.
The hydroxyl number of component (i), L.e., of the product from the reaction of a melamine- coinitiator mixture with alkylene oxide, is between 1000 and 20 mg KOH/g, preferably between 100 and 800 mg KOH/g and more preferably between 300 and 600 mg KOH/g.
In one embodiment of the process according to the present invention, the polyether alcohol component (if) is obtainable by reacting at least one compound selected from the group comprising sucrose, glycerol, ethylene glycol, diethylene glycol, propylene glycal, dipropylene glycol, 1,4-butanediol, pentaerythritol, trimethylolpropane, water, sorbitol, urea, biuret, EDA,
TDA, MDA and combinations thereof, with at least one alkylene oxide.
In a further embodiment of the process according to the present invention, the alkylene oxide used for obtaining the polyether alcohol component (ji) is selected from the group comprising propylene oxide and mixtures of propylene oxide with ethylene oxide.
In one embodiment of the process according to the present invention, the component (iii) is a polyether alcohol component obtainable by reacting aliphatic and/or aromatic amines with ethylene oxide and/or propylene oxide.
An aromatic amine is used under (ji) in one embodiment, Vicinal tolylenediamine is preferably used in this case.
An aliphatic amine is used under (jii} in a further embodiment. Ethylenediamine is preferably used in this case. tn a further embodiment of the process according to the present invention, component (iii) is a 40 polyether alcohol component obtainable by reaction of glycerol and/or trimethylolpropane (TMP) with ethylene oxide and/or propyiene oxide.
In one embodiment of the process according to the present invention, component (iii) is a polyether alcohol component selected from the group comprising alkylene oxide addition products of sugar, glycerol, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,4-butanediocl, pentaerythritol, frimethylolpropane, water or sorbitol or combinations thereof, preferably glycerol, ethylene glycol, diethylene glycol, propylene glycol and dipropylene glycol.
In a further embodiment of the process according fo the present invention, component (iii) is a polyester alcohol component (ji) selected from the group comprising condensation products of adipic acid, terephthalic acid, isophthalic acid, succinic acid, with difunctional alcohols selected from the group comprising ethylene glycol and 1,4-butanediol.
The proportion of component (i), based on (i)+(ii)+(iii}, is preferably between 10% and 40% by weight.
The proportion of component (ii), based on (i)+(ii)+(iii), is preferably between 30% and 60% by weight.
In a preferred embodiment of the process according to the present invention, the polyether alcohol component (i} has a hydroxyl number in the range between 300-600 mg KOH/g and is obtainable by reacting a mixture of melamine and a further hydroxyl- and/or amino-functional compound, in a mass ratio ranging from 3:2 to 2:3 and a mixture functionality ranging from 4 to 8, with propylene oxide and/or propylene oxide/ethylene oxide mixtures, and the polyether alcohol component (ii) is obtainable by addition of propylene oxide and/or propylene oxidefethylene oxide mixtures onto tolylenediamine, and the further compound (iii) is a polyether alcohol component having a functionality of 2 to 3 and a hydroxyl number in the range between 100 and 300 mg KQH/g and is obtainable by addition of propylene oxide and/or propylene oxide/ethylene oxide mixtures onto glycerol, ethylene glycol, diethylene glycol, propylene glycol or dipropylene glycol or mixtures thereof.
In one embodiment of the process according fo the present invention, the at least one polyisocyanate (a) is selected from the group comprising aromatic, aliphatic and cycloaliphatic polyisocyanates.
Here the term “polyisocyanate” for the purposes of this invention comprises compounds having two or more isocyanate groups, for example diphenylimethane diisocyanate (MD}), tolylene diisocyanate (TDI), tri-, tetra-, penta-, hexa-, hepta- and/or octamethylene diisocyanate, 2— methylpentamethyiene 1,5-diisocyanate, 2-ethylbutylene 1,4-dlisocyanate, 1-isocyanato-3,3,5- trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate, 1PDI), 1,4- and/or 1,3- 40 bis(isocyanatomethyl)cyclohexane (HXDI), 1,4—cyclohexane diisocyanate, 1—-methyl-2,4- and/or -2,6-cyclohexane diisocyanate, 4,4'-, 2,4'- and/or 2,2'dicyclohexylmethane diisocyanate; preference is given to the use of MDI and/or TDI.
in one embodiment of the process according to the present invention, the at least one blowing agent {b) is selected from the group comprising physical blowing agents and chemical blowing : agents. ltis preferable to use exactly one physical blowing agent and exactly one chemical blowing agent.
In combination with or in place of chemical blowing agents, physical blowing agents can also be used. Physical blowing agents are compounds which are inert with regard to the use components, usually liquid at room temperature and vaporize under the conditions of the urethane reaction. The boiling point of these compounds is preferably below 50°C. Useful physical blowing agents also include compounds that are gaseous at room temperature and are introduced into and/or dissolved in the use components under pressure, for example carbon dioxide, low-boiling alkanes and fluoroalkanes.
Physical biowing agents are usually selected from the group comprising alkanes and/or cycloalkanes having at least 4 carbon atoms, dialkyl ethers, esters, ketones, acetals, fluoroalkanes having 1 to 8 carbon atoms, and tetraalkyisilanes having 1 to 3 carbon atoms in the alkyl chain, more particularly teframethylsilane.
In one preferred embodiment of the invention, the blowing agents (¢) are hydrocarbons. The blowing agents are more preferably selected from the group comprising alkanes and/or cycloalkanes having at least 4 carbon atoms. Pentanes are used in particular, preferably isopentane and cyclopentane. When the rigid foams are used as insulation in refrigerating appliances, cyclopentane is preferred. The hydrocarbons can be used in admixture with water.
Examples of blowing agents (¢) useful according to the present invention are propane, n- butane, isobutane, cyclobutane, n-pentane, isopentane, cyclopentane, cyclohexane, dimethyl ether, methyl ethyl ether, methyl butyl ether, methyl formate, acetone, and also fluoroalkanes which can be degraded in the troposphere and therefore are harmiess to the ozone layer, such as trifluoromethane, difluoromethane, 1,1,1,3,3-pentafluorobutane, 1,1,1,3,3-pentafiucro- propane, 1,1,1,2-tetrafluorcethane, difluoroethane and 1,1,1,2,3,3,3-heptafluoropropane, and also perflucroalkanes, such as CsFs, CaFio, CsF12, CeF14, and C7F 1s. The physical blowing agents mentioned can be used alone or in any desired combination with each or one another.
Useful blowing agents further include hydrofluorolefins, such as 1,3,3,3-tetrafluoropropene, or hydrochlorofiuorolefing, such as 1-chloro-3,3,3-triflucropropene. Blowing agents cf this type are described in WO 2009/0488286 for example. 40 Water is used as chemical blowing agent in a preferred embodiment where it reacts with isocyanate groups to eliminate carbon dioxide. Formic acid can also be used for example as physical blowing agent.
Polyurethane rigid foams are obtainable according to the present invention in the presence or absence of catalysts, flame retardants and also customary auxiliary and/or addition agents, o> As catalysts there are more particularly used compounds which substantially speed the reaction of the isocyanate groups with the isocyanate-reactive groups.
Such catalysts are strong basic amines, for example secondary aliphatic amines, imidazoles, amidines, and also alkanolamines or organometallic compounds, more particularly organotin compounds.
When the polyurethane rigid foam is to incorporate isocyanurate groups as well, specific catalysts are needed. As isocyanurate catalysts there are typically used metal carboxylates, more particularly potassium acetate and its solutions.
The catalysts can be used either alone or in any desired mixtures, as required,
As auxiliaries and/or additive agents there are used the substances known per se for this purpose, examples being surface-active substances, foam stabilizers, cell regulators, fillers, pigments, dyes, flame retardants, hydrolysis control agents, antistats, fungistatically and bacteriostatically active agents.
Further particulars concerning starting compounds used are given for example in
Kunststoffhandbuch, volume 7, “Polyurethanes,”, edited by Glinter Oertel, Carl-Hanser-Verlag,
Munich, 3 edition, 1993.
The paragraphs which follow give some examples to illustrate some aspects of the present invention. These examples shall in no way be deemed fo restrict the scope of the invention.
Synthesis example 1: 1.44 kg of melamine are initially charged to a 20 L steel autoclave together with 1.44 kg of glycerol and the reaction mixture is heated to 160°C under agitation. After the reaction temperature has been reached, 11.51 kg of propylene oxide are added over 6 hours. This is followed by a five-hour secondary reaction until the pressure assumes a constant value. Then, the crude product is freed of residual monomer and other volatile components at 15 mbar and 160°C for 60 minutes to obtain 14 kg of a slightly yellowish viscous liquid.
Hydroxyl value: 487 mg KOH/g (DIN 53240) 40 Viscosity (at 25°C): 2161 mPas (DIN 51550)
Synthesis example 2:
1.2 kg of melamine are initially charged to a 20 L steel autoclave together with 1.8 kg of trimethylolpropane and the reaction mixture is heated to 160°C under agitation. After the reaction temperature has been reached, 9.69 kg of propylene oxide are added over 7 hours.
This is followed by a six-hour secondary reaction until the pressure assumes a constant value.
Then, the crude product is freed of residual monomer and other volatile components at 15 mbar and 160°C for 60 minutes to obtain 12 kg of a slightly yellowish viscous liquid.
Hydroxyi value: 490 mg KOH/g (DIN 53240)
Viscosity (at 25°C): 4996 mPas (DIN 51550)
Synthesis example 3: 1.44 kg of melamine are initially charged to a 20 L steel autoclave together with 1.44 kg of sorbitol and the reaction mixture is heated to 160°C under agitation. After the reaction temperature has been reached, 11.5 kg of propylene oxide are added over 10 hours. This is followed by a seven-hour secondary reaction until the pressure assumes a constant value.
Then, the crude product is freed of residual monomer and other volatile components at 15 mbar and 160°C for 60 minutes to obtain 14 kg of a slightly yellowish viscous liquid.
Hydroxyl value: 466 mg KOH/g (DIN 53240)
Viscosity (at 25°C): 4013 mPas (DIN 51550)
Use examples:
The products obtained according to synthesis examples 1, 2 and 3 were used in polyurethane rigid foam formulations and compared with a reference system.
Raw materials used:
Polyol A: polyether alcohol from sucrose, glycerol and propylene oxide, functionality 5.1, hydroxyl number 450, viscosity 20 000 mPa.s at 25°C
Polyol B: polyether alcohol from vicinal TDA, ethylene oxide and propylene oxide, ethylene oxide content: 15%, functionality 3.8, hydroxyl number 390, viscosity 13 000 mPa.s at 25°C Polyol C: polyether alcohol from vicinal TDA, ethylene oxide and propylene oxide, ethylene oxide content: 15%, functionality 3.9, hydroxyl number 180, viscosity 650 mPa.s at 25°C
Stabilizer: Tegostab® B 8462 (silicone stabilizer from Evonik)
Catalyst 1: dimethylcyciohexylamine (BASF) 40 Catalyst 2: pentamethyidiethyienetriamine (BASF)
Catalyst 3: N,N',N"-fris(dimethylaminopropyl)-s-hexahydrotriazine (BASF) isocyanate: polymer MDI (Lupranat® M20, BASF)
Machine foaming:
The stated raw materials were used to obtain a polyol component. Using a high pressure Puromat® PU 30/80 IQ (BASF Polyurethanes GmbH) with an application rate of 250 g/sec., the polyol component was mixed with the requisite amount of the stated isocyanate, so that an isocyanate index of 116.7 was obtained (unless otherwise stated). The reaction mixture was injected into heated molds of dimensions 2000 mm x 200 mm x 50 mm and 400 mm x 700 mm x 90 mm and allowed to foam up therein. Overpacking was 15%.
1 (reference) 2 (wt%) 3 (wt%) 4 (wt%)
EE 5 a a povos [sm | 0 | oo | 0 pobolofeample | 0 | | 0 | 0 [boboiofexemplez | 0 | 0 | sw | 0 povolofeamples | 0 | 0 | 0 | a viscosity of polyol 8400 6000 5300 6100 pt I I Ml minimum fill density 30.8 flow index (min. fill 1.34 1.34 1.34 1.35 arm] | |] thermal conductivity 19.7 19.9 18.7 19.7 go | 7 | mR compressive strength 15.6 16.8 17.4 17.0 (density 31) 15% OP,
Ea I I
Example 1 is a comparative exampie. The systems in examples 2, 3 and 4 (al in accordance with the present invention), featuring melamine alcohols based on melamine, a coinitiator and propylene oxide, have distinctly improved mechanical stability, which manifests in increased compressive strength. Furthermore, the viscosities of the polyol mixtures are distinctly lower than in the comparative example.
Claims (1)
- We claim:-1. A process for producing polyurethane rigid foams, which comprises (a) reacting at least one polyisocyanate by using (b) at least one blowing agent with (c) three or more different compounds each having two or more isocyanate-reactive hydrogen atoms, wherein (i) one of the three or more different compounds each having two or more isocyanate-reactive hydrogen atoms is a polyether alcohol component obtainable by reacting a mixture of melamine and at least one further hydroxyl and/or amino-functional compound having a functionality ranging from 2 fo 8 with at least one alkylene oxide, and (if) a further one of the three or more different compounds each having two or more isocyanate-reactive hydrogen atoms is a polyether alcohol component having a hydroxyl number of 300 to 600 mg KOH/g coupled with an average functionality of 4 to 8, and (ii) the third one of the three or more different compounds each having two or more isacyanate-reactive hydrogen atoms is a polyether alcohol and/or polyester alcohol component having a hydroxy! number of 100 to 350 mg KOH/g coupled with an average functionality of 2 to 5.2. The process for producing polyurethane rigid foams according to claim 1 wherein the polyether alcohol companent (i) is obtained without a catalyst.3. The process for producing polyurethane rigid foams according to claim 1 or 2 wherein the polyether alcohol component (i) is obtainable by reacting a mixture of melamine and a further hydroxyl- and/or amino-~functional compound in a mass ratio ranging from 3:1 fo 1:3 and a mixture functionality in the range from 4 to 6, with at least one alkylene oxide. 4, The process for producing polyurethane rigid foams according to any one of claims 1 to 3 wherein the polyether alcohol component (i) is obtainable by reacting a mixture of melamine and a further hydroxyl- and/or amino-functional compound selected from the group comprising glycerol, propylene glycol, ethylene glycol, dipropyiene glycol, diethylene glycol, trimethylolpropane, sorbitol, urea, biuret, triethanolamine, diethanolamine, ethanolamine, triisopropanolamine, diisopropanolamine, isopropanclamine, ethylenediamine (EDA), tolylenediamine (TDA) and methylenedianiline (MDA), with at least one alkylene oxide.5. The process for producing polyurethane rigid foams according to any one of claims 1 to 4 wherein the at least one alkylene oxide under (i) is selected from the group comprising propylene oxide, ethylene oxide, 1,2-butylene oxide and styrene oxide.8. The process for producing polyurethane rigid foams according to any one of claims 1 to 40 5 wherein the alkylene oxide under (i) is selected from the group comprising propylene oxide and propylene oxide/ethylene oxide mixtures.7. The process for producing polyurethane rigid foams according to any one of claims 1 to 8 wherein the polyether alcohol component (i) is obtained in a temperature range between 120 and 180°C.8. The process according to any one of claims 1 to 7 wherein the polyether alcohol component (ii) is obtainable by reacting at least one compound selected from the group comprising sucrose, glycerol, ethylene glycol, diethylene giycol, propylene glycol, dipropylene glycol, 1,4-butanediol, pentaerythritol, trimethylolpropane, water, sorbitol, urea, biuret, EDA, TDA, MDA and combinations thereof, with at least one alkylene oxide.0. The process according to any one of claims 1 to 8 wherein the alkylene oxide used for obtaining the polyether alcohol component (ii) is selected from the group comprising propylene oxide and mixtures of propylene oxide with ethylene oxide.10. The process for producing polyurethane rigid foams according to any one of claims 1 to 9 wherein the component (ji) is a polyether alcohol component obtainable by reacting aliphatic and/or aromatic amines with ethylene oxide and/or propylene oxide.11. The process for producing polyurethane rigid foams according to claim 10 wherein an aromatic amine is used under (iii).12. The process for producing polyurethane rigid foams according to claim 41 wherein the aromatic amine under (iii) is vicinal tolylenediamine.13. The process for producing polyurethane rigid foams according to claim 10 wherein an aliphatic amine is used under (iii).14. The process for producing polyurethane rigid foams according to claim 13 wherein the aliphatic amine under (iii) is ethylenediamine.18. The process for producing polyurethane rigid foams according to any one of claims 1 to 9 wherein the component (iil) is a polyether alcohol component obtainable by reaction of glycerol and/or trimethylolpropane with ethylene oxide and/or propylene oxide.16. The process according to any one of claims 1 to 15 wherein the proportion of component (i), based on (i}+(ii)+(iif), is between 10% and 40% by weight.17. The process according to any one of claims 1 to 16 wherein the proportion of component (ii), based on (i}+(ii}+(i}), is between 30% and 60% by weight. 4018. The process for producing polyurethane rigid foams according to any one of claims 1 to 17 wherein the at least one polyisocyanate (a) is selected from the group comprising aromatic, aliphatic and cycloaliphatic polyisocyanates.19. The process for producing polyurethane rigid foams according to any one of claims 1 to 18 wherein the at least one blowing agent (b) is selected from the group comprising physical blowing agents and chemical blowing agents. S20. A polyurethane rigid foam obtainable by the process of any one of claims 1 to 19.21. The use of a polyurethane rigid foam obtainable by the process of any one of claims 1 to 19 as thermal insulating material in refrigerating appliances, hot water storage systems, district heating pipes or building construction.
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EP11161426 | 2011-04-07 | ||
PCT/EP2012/055922 WO2012136608A1 (en) | 2011-04-07 | 2012-04-02 | Method for producing rigid pu foam materials |
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JP (1) | JP6034363B2 (en) |
KR (1) | KR20140020974A (en) |
CN (1) | CN103459451B (en) |
BR (1) | BR112013019599A2 (en) |
HU (1) | HUE027529T2 (en) |
MX (1) | MX346128B (en) |
PL (1) | PL2694564T3 (en) |
RU (1) | RU2597931C2 (en) |
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PT2697280E (en) * | 2011-04-15 | 2015-09-09 | Basf Se | Process for producing rigid polyurethane foams |
US9403963B2 (en) | 2011-08-23 | 2016-08-02 | Basf Se | Particle-comprising polyether alcohols |
US10100513B2 (en) | 2012-11-05 | 2018-10-16 | Basf Se | Process for producing profiled elements |
US8987518B2 (en) | 2013-02-28 | 2015-03-24 | Basf Se | Polyamines and process for preparation thereof |
BR112019010988A2 (en) * | 2016-11-29 | 2019-10-15 | Covestro Deutschland Ag | rigid polyurethane foam, method for producing and using |
CN107513157B (en) * | 2017-09-15 | 2021-02-02 | 万华化学集团股份有限公司 | Amino polyether polyol and preparation method and application thereof |
CN109306054A (en) * | 2018-09-28 | 2019-02-05 | 山东诺威新材料有限公司 | Full water spray coating foaming flame retardant polyether polyol and preparation method thereof |
CN113698587A (en) * | 2021-09-08 | 2021-11-26 | 航锦科技股份有限公司 | Preparation method of hard foam polyether polyol |
CN113754878B (en) * | 2021-09-10 | 2024-04-12 | 山东一诺威新材料有限公司 | Synthesis method of polyaniline-based polyether polyol |
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US4939182A (en) * | 1988-07-27 | 1990-07-03 | The Dow Chemical Company | Melamine-alkanolamine condensates and polyurethanes prepared therefrom |
JP3072309B2 (en) * | 1995-09-06 | 2000-07-31 | 三洋化成工業株式会社 | Manufacturing method of rigid polyurethane foam |
DE19723193A1 (en) * | 1997-06-03 | 1998-12-10 | Bayer Ag | Process for the production of closed-cell rigid polyurethane foams with low thermal conductivity |
DE19905573A1 (en) * | 1999-02-11 | 2000-08-17 | Bayer Ag | Polyurethane hard foam material useful for defoaming hollow spaces in cooling unit contains mixture of diphenylmethane diisocyanate and polyphenylpolymethylene polyisocyanate |
DE10015001A1 (en) | 2000-03-25 | 2001-09-27 | Basf Ag | Isocyanate based hard foamed plastics useful for hot and cold insulation devices and in insulating sandwich elements, have good flowability without impairment of their mechanical properties |
US6846850B2 (en) * | 2003-01-22 | 2005-01-25 | Bayer Materialscience Llc | Rigid polyurethane foams with improved properties |
WO2008058863A1 (en) | 2006-11-14 | 2008-05-22 | Basf Se | Method for the production of rigid polyurethane foams |
EP2085412B1 (en) * | 2006-11-20 | 2014-06-18 | Asahi Glass Company, Limited | Method for producing hard polyurethane foam and hard polyurethane foam |
RU2339663C1 (en) * | 2007-06-05 | 2008-11-27 | Федеральное казенное предприятие (ФКП) "Пермский пороховой завод" | Polyol composition for obtaining rigid foamed polyurethanes of heat insulation purpose |
US9453115B2 (en) | 2007-10-12 | 2016-09-27 | Honeywell International Inc. | Stabilization of polyurethane foam polyol premixes containing halogenated olefin blowing agents |
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JP6034363B2 (en) | 2016-11-30 |
EP2694564A1 (en) | 2014-02-12 |
CN103459451A (en) | 2013-12-18 |
EP2694564B1 (en) | 2015-06-17 |
BR112013019599A2 (en) | 2017-01-31 |
MX2013010318A (en) | 2013-10-28 |
KR20140020974A (en) | 2014-02-19 |
HUE027529T2 (en) | 2016-11-28 |
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JP2014511918A (en) | 2014-05-19 |
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