JP5933442B2 - 1,3−及び/又は1,4−ビス(アミノメチル)シクロヘキサン開始ポリオールとメチレンビス(シクロヘキシルアミン)開始ポリオール及びシクロヘキサンジアミン開始ポリオールの内の少なくとも1つとを含有するポリオール混合物、並びにそれらから製造されたポリウレタン - Google Patents
1,3−及び/又は1,4−ビス(アミノメチル)シクロヘキサン開始ポリオールとメチレンビス(シクロヘキシルアミン)開始ポリオール及びシクロヘキサンジアミン開始ポリオールの内の少なくとも1つとを含有するポリオール混合物、並びにそれらから製造されたポリウレタン Download PDFInfo
- Publication number
- JP5933442B2 JP5933442B2 JP2012532129A JP2012532129A JP5933442B2 JP 5933442 B2 JP5933442 B2 JP 5933442B2 JP 2012532129 A JP2012532129 A JP 2012532129A JP 2012532129 A JP2012532129 A JP 2012532129A JP 5933442 B2 JP5933442 B2 JP 5933442B2
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- JP
- Japan
- Prior art keywords
- polyol
- bis
- cyclohexane
- mixture
- aminomethyl
- 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.)
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- 229920005862 polyol Polymers 0.000 title claims description 126
- 150000003077 polyols Chemical class 0.000 title claims description 125
- 229920005903 polyol mixture Polymers 0.000 title claims description 48
- YZOISHTVEWVNHA-UHFFFAOYSA-N n,n'-dicyclohexylmethanediamine Chemical compound C1CCCCC1NCNC1CCCCC1 YZOISHTVEWVNHA-UHFFFAOYSA-N 0.000 title claims description 22
- OXIKYYJDTWKERT-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCC(CN)CC1 OXIKYYJDTWKERT-UHFFFAOYSA-N 0.000 title claims description 19
- 229920002635 polyurethane Polymers 0.000 title claims description 12
- 239000004814 polyurethane Substances 0.000 title claims description 12
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 title description 12
- 239000000203 mixture Substances 0.000 claims description 104
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 68
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000003999 initiator Substances 0.000 claims description 35
- 239000005056 polyisocyanate Substances 0.000 claims description 30
- 229920001228 polyisocyanate Polymers 0.000 claims description 30
- -1 1,2-diaminocyclohexane compound Chemical class 0.000 claims description 27
- 150000001412 amines Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 22
- 239000004604 Blowing Agent Substances 0.000 claims description 21
- 229920005830 Polyurethane Foam Polymers 0.000 claims description 20
- 239000011496 polyurethane foam Substances 0.000 claims description 20
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 229920000570 polyether Polymers 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 10
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 150000001983 dialkylethers Chemical class 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 238000002347 injection Methods 0.000 claims description 5
- 239000007924 injection Substances 0.000 claims description 5
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 3
- UKQUQELUEZHUEP-UHFFFAOYSA-N 2-[(2-amino-4-methylcyclohexyl)methyl]-5-methylcyclohexan-1-amine Chemical compound NC1CC(C)CCC1CC1C(N)CC(C)CC1 UKQUQELUEZHUEP-UHFFFAOYSA-N 0.000 claims description 2
- VYAFHUCZHUIBPY-UHFFFAOYSA-N 2-[(2-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound NC1CCCCC1CC1C(N)CCCC1 VYAFHUCZHUIBPY-UHFFFAOYSA-N 0.000 claims description 2
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 claims description 2
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 claims description 2
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 claims description 2
- NTGJOYPFNABNES-UHFFFAOYSA-N 4-[(4-amino-2-methylcyclohexyl)methyl]-3-methylcyclohexan-1-amine Chemical compound CC1CC(N)CCC1CC1C(C)CC(N)CC1 NTGJOYPFNABNES-UHFFFAOYSA-N 0.000 claims 1
- 229940126062 Compound A Drugs 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical compound NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 claims 1
- 239000006260 foam Substances 0.000 description 92
- 238000009472 formulation Methods 0.000 description 52
- 239000003054 catalyst Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 125000001424 substituent group Chemical group 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 150000004665 fatty acids Chemical class 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 11
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 11
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 229920013701 VORANOL™ Polymers 0.000 description 10
- 238000009413 insulation Methods 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 10
- 150000002513 isocyanates Chemical class 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 9
- 125000004185 ester group Chemical group 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 description 7
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 229920001451 polypropylene glycol Polymers 0.000 description 6
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 5
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229920005906 polyester polyol Polymers 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000000600 sorbitol Substances 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical group NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical group OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 150000003335 secondary amines Chemical group 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- OTJFQRMIRKXXRS-UHFFFAOYSA-N (hydroxymethylamino)methanol Chemical compound OCNCO OTJFQRMIRKXXRS-UHFFFAOYSA-N 0.000 description 2
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 description 2
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 description 2
- FRCHKSNAZZFGCA-UHFFFAOYSA-N 1,1-dichloro-1-fluoroethane Chemical compound CC(F)(Cl)Cl FRCHKSNAZZFGCA-UHFFFAOYSA-N 0.000 description 2
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-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
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical group CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical group NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 2
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000019737 Animal fat Nutrition 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-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
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000012963 UV stabilizer Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical group NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 2
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical group CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 2
- 229940043276 diisopropanolamine Drugs 0.000 description 2
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- 150000002148 esters Chemical class 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 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 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 150000001261 hydroxy acids Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 2
- 229940087646 methanolamine Drugs 0.000 description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical group OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
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- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- LVPSBELIABHESA-UHFFFAOYSA-L zinc;n,n-dibutylcarbamothioate Chemical compound [Zn+2].CCCCN(C([O-])=S)CCCC.CCCCN(C([O-])=S)CCCC LVPSBELIABHESA-UHFFFAOYSA-L 0.000 description 1
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- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
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Description
a)少なくとも
1)第1態様において記載したポリオール混合物と、
2)少なくとも1つの炭化水素、ヒドロフルオロカーボン、ヒドロクロロフルオロカーボン、フルオロカーボン、ジアルキルエーテル若しくはフッ素置換ジアルキルエーテル物理的発泡剤と、
3)少なくとも1つのポリイソシアネートと、
を含有する反応混合物を形成する工程と、
b)該反応混合物を、該反応混合物が膨張及び硬化して硬質ポリウレタンフォームを形成する条件にかける工程と
を含む方法である。
によって表すことができる。構造Iは1,3−異性体を表し、構造IIは1,4−異性体を表す。
によって表すことができる。NH2基は、2、3又は4位にあってよい。2個のNH2基は、中心メチレンに対して対称性又は非対称性に位置してよい。好ましい異性体は、2,2’、4,4’及び2,4’異性体である。
によって表すことができるポリエーテルである。少なくとも3個のA基は(CxHyO)zH基であってよく、全4個のA基は(CxHyO)zH基であってよい。−N(A)2基は、1位として−N(A)2基の1つの位置を取る1,2−、1,3−及び/又は1,4位にあってよい。
によって表されるシクロヘキサンジアミン開始剤化合物から調製できる。上記の構造に対応する2つ又は開始剤化合物の混合物を使用できる。
1.ヒマシ油。
2.国際公開第2004/096882号パンフレット及び第2004/096883号パンフレットに記載されたヒドロキシメチル基含有ポリオール。そのようなポリオールは、12〜26個の炭素原子を有するヒドロキシメチル基含有脂肪酸、又はそのようなヒドロキシル基含有脂肪酸のエステルを平均して少なくとも2個のヒドロキシル、第1級及び/又は第2級アミノ基を有するポリオール若しくはポリアミン開始剤化合物と、該ヒドロキシメチル基含有ポリエステルポリオールが開始剤化合物上のヒドロキシル、第1級アミン及び第2級アミン基の総数当たり該ヒドロキシメチル基含有脂肪酸若しくはエステルに由来する平均して少なくとも1.3繰り返し単位を含有し、該ヒドロキシメチル基含有ポリエステルポリオールが少なくとも400〜15,000までの当量を有するように反応させる工程によって調製される。好ましいそのようなポリオールは、下記の平均構造:
(式中、Rは、n個のヒドロキシル及び/又は第1級又は第2級アミン基を有する開始剤化合物の残基であり、nは、少なくとも2である;各Xは、独立して−O−、−NH−若しくは−NR’−(式中、R’は、不活性に置換されたアルキル、アリール、シクロアルキル、若しくはアラルキル基である)であり、pは、1〜ヒドロキシメチル含有ポリエステルポリオール1分子当たりの[X−Z]基の平均数を表すnの数であり、Zは、1個又はそれ以上のA基を含有する直鎖若しくは分子鎖であるが、ただし1分子当たりのA基の平均数は≧1.3nであり、各Aは独立して、少なくとも一部のA基がA1、A2又はA3であることを前提にA1、A2、A3、A4及びA5から成る群から選択されることを前提とするが、このときA1は:
によって表すことができる。各−R−O−C(O)−結合は、上記で考察した第1タイプのエステル基を表す。R1鎖の少なくとも一部分は以下:
で表すことのできる少なくとも1個のヒドロキシル含有エステル基で置換されている。この構造の左に示した結合は、脂肪酸鎖の炭素原子に付着する。この状況における不活性置換基は、この物質の形成又はポリウレタンを製造する際のその使用を妨害しない置換基である。
好ましい実施形態では、ポリオール混合物は、(即ち、成分(a)及び(b)に加えて)1分子当たり4.5〜7個のヒドロキシル基の平均官能価及び100〜175のヒドロキシル当量を有する少なくとも1つの他のポリエーテルポリオールを含有する。その他のポリエーテルポリオールは、例えば、ソルビトール開始又はスクロース/開始−開始ポリエーテルであってよい。使用できる適切なソルビトール開始又はスクロース/開始−開始ポリエーテルの例には、全部がDow Chemical社から入手できるVoranol(登録商標)360、Voranol(登録商標)RN411、Voranol(登録商標)RN490、Voranol(登録商標)370、Voranol(登録商標)446、Voranol(登録商標)520、Voranol(登録商標)550及びVoranol(登録商標)482ポリオールが含まれる。
有機酸と様々な金属との塩、四価スズ、三価及び五価のAs、Sb及びBiの有機金属誘導体並びに鉄及びコバルトの金属カルボニルが含まれる。
28モルのメチレンビス(シクロヘキシルアミン)が窒素雰囲気下で反応容器に加えられる。容器及びその内容物は、125℃に加熱され、85モルのプロピレンオキシドが供給される。反応混合液は4時間に渡り125℃で消化させられ、その時点に82gの45重量%の水酸化カリウム溶液が加えられる。水は次に真空下で除去され、72モルのプロピレンオキシドが反応器内に供給される。反応混合物は再び4時間に渡り125℃で消化させられ、その時間後に酢酸溶液が加えられる。生成物のメチレンビス(シクロヘキシルアミン)開始ポリオールは、415mg KOH/gのヒドロキシル価及び50℃で73,000cpsの粘度を有する。
硬質ポリウレタンフォームは、表1に記載した成分から製造する。フォームの加工処理は、175〜225g/秒のスループットで作動させるHi Tech CS−50高圧機械を使用して実施する。フォーム配合物は、(自由上昇密度を測定するための)バッグ内及び45℃に予熱した垂直Brett型内に注入する。混合する工程前の成分の温度は、約21℃である。
硬質ポリウレタンフォームは、表2に記載した成分から、実施例1に記載した方法と同一方法で製造し、先行実施例に記載したように試験する。結果は表2に報告した通りである。比較例Aについてのデータは、比較のために表2にも複製されている。
Claims (7)
- (a)少なくとも1つのC2−C4アルキレンオキシドと、1,3−ビス(アミノメチル)シクロヘキサン及び1,4−ビス(アミノメチル)シクロヘキサンからなる群より選択される少なくとも一つとの反応生成物である、3.0超〜4.0の平均ヒドロキシル官能価を有する少なくとも1つのアミン開始ポリオールと、
(b)(i)及び(b)(ii)の内の少なくとも1つであって、(b)(i)は少なくとも1つのC2−C4アルキレンオキシドとメチレンビス(シクロヘキシルアミン)開始剤化合物との反応生成物である、3.0超〜4.0の平均ヒドロキシル官能価を有する少なくとも1つのアミン開始ポリオールであり、(b)(ii)は少なくとも1つのC2−C4アルキレンオキシドと、1,2−ジアミノシクロヘキサン化合物、1,3−ジアミノシクロヘキサン化合物及び1,4−ジアミノシクロヘキサン化合物からなる群より選択される少なくとも一つとの反応生成物である、3.0超〜4.0の平均ヒドロキシル官能価を有する少なくとも1つのアミン開始ポリオールである(b)とを含むポリオール混合物であって、
(i)成分(a)及び(b)の各々は、前記ポリオール混合物中の少なくとも0.5重量%のポリオールを構成し、
(ii)成分(a)及び(b)は一緒に前記ポリオール混合物中の少なくとも2重量%のポリオールを構成し、
(iii)成分(a)及び(b)は各々、3.3〜4.0のヒドロキシル官能価及び75〜560のヒドロキシル当量を有し、
(iv)前記ポリオール混合物がさらに、(A)4.5〜7のヒドロキシル官能価及び100〜175のヒドロキシル当量を有する少なくとも1つのポリエーテルポリオールと、(B)2.0〜4.0の平均ヒドロキシル官能価及び100〜225のヒドロキシル当量を有する少なくとも1つの追加のトルエンジアミン開始ポリオールと、(C)2.0〜3.0のヒドロキシル官能価及び90〜500のヒドロキシル当量を有する非アミン開始ポリオールとを含有する、ポリオール混合物。 - 前記メチレンビス(シクロヘキシルアミン)開始剤化合物は、メチレンビス(4−アミノシクロヘキサン)、メチレンビス(2−アミノシクロヘキサン)、2,4’−ジアミノ−メチレンビス(シクロヘキサン)、メチレンビス(4−アミノ−2−メチル−シクロヘキサン)、メチレンビス(2−アミノ−4−メチル−シクロヘキサン)、メチレンビス(4−アミノ−3−メチル−シクロヘキサン)である、請求項1に記載のポリオール混合物。
- 前記1,3−ビス(アミノメチル)シクロヘキサン及び1,4−ビス(アミノメチル)シクロヘキサンからなる群より選択される少なくとも一つは、1,3−ビス(アミノメチル)シクロヘキサン、1,4−ビス(アミノメチル)シクロヘキサン、又は1,3−ビス(アミノメチル)シクロヘキサン及び1,4−ビス(アミノメチル)シクロヘキサンの混合物である、請求項1又は2に記載に記載のポリオール混合物。
- 前記アルキレンオキシドは、エチレンオキシド、プロピレンオキシド、又はエチレンオキシド及びプロピレンオキシドの混合物である、請求項1から3のいずれか一項に記載のポリオール混合物。
- ポリウレタンを製造するための方法であって、請求項1から4のいずれかに記載のポリオール混合物を少なくとも1つのポリイソシアネートと、前記ポリオール混合物が前記ポリイソシアネートと反応してポリウレタンを形成する条件下で接触させる工程を含む方法。
- 真空支援注入法である、請求項5に記載の方法。
- 硬質ポリウレタンフォームを製造するための方法であって、
a)少なくとも
1)請求項1から4のいずれか一項に記載のポリオール混合物と、
2)少なくとも1つの炭化水素、ヒドロフルオロカーボン、ヒドロクロロフルオロカーボン、フルオロカーボン、ジアルキルエーテル若しくはフッ素置換ジアルキルエーテル物理的発泡剤と、
3)少なくとも1つのポリイソシアネートと、
を含有する反応混合物を形成する工程と、
b)前記反応混合物を、前記反応混合物が膨張及び硬化して硬質ポリウレタンフォームを形成する条件にかける工程と
を含む方法。
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US24674209P | 2009-09-29 | 2009-09-29 | |
US61/246,742 | 2009-09-29 | ||
PCT/US2010/049571 WO2011041163A1 (en) | 2009-09-29 | 2010-09-21 | Polyol mixtures containing a 1,3-and/or 1,4-bis(aminomethyl) cyclohexane-initiated polyol and at least one of a methylene bis (cyclohexylamine)-initiated polyol and a cyclohexanediamine-initiated polyol, and polyurethanes made therefrom |
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JP5933442B2 true JP5933442B2 (ja) | 2016-06-08 |
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JP2012532129A Active JP5933442B2 (ja) | 2009-09-29 | 2010-09-21 | 1,3−及び/又は1,4−ビス(アミノメチル)シクロヘキサン開始ポリオールとメチレンビス(シクロヘキシルアミン)開始ポリオール及びシクロヘキサンジアミン開始ポリオールの内の少なくとも1つとを含有するポリオール混合物、並びにそれらから製造されたポリウレタン |
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US (1) | US20120172470A1 (ja) |
EP (1) | EP2483325B1 (ja) |
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KR (1) | KR101837207B1 (ja) |
CN (1) | CN102666627B (ja) |
BR (1) | BR112012006812A2 (ja) |
ES (1) | ES2447292T3 (ja) |
MX (1) | MX2012003741A (ja) |
WO (1) | WO2011041163A1 (ja) |
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ES2378504T3 (es) * | 2008-06-10 | 2012-04-13 | Dow Global Technologies Inc. | Procedimiento para preparar una espuma rígida de poliuretano a partir de polioles iniciados con metilenbis(ciclohexilamina) |
ES2792351T3 (es) * | 2008-06-10 | 2020-11-11 | Dow Global Technologies Llc | Polioles iniciados con 1,3- o 1,4-bis(aminometil)ciclohexano y espuma de poliuretano rígida obtenida a partir de ellos |
CA2839446C (en) * | 2011-06-27 | 2020-01-21 | Owens Corning Intellectual Capital, Llc | Organic infrared attenuation agents |
EP3458492A4 (en) * | 2016-05-20 | 2020-02-19 | Covestro Deutschland AG | POLYURETHANE FOAM AND POLYURETHANE COMPOSITE CONTAINING THE SAME |
JP6909074B2 (ja) * | 2017-06-28 | 2021-07-28 | サンスター技研株式会社 | ポリウレタン組成物 |
WO2019194966A1 (en) * | 2018-04-03 | 2019-10-10 | Dow Global Technologies Llc | Foam formulations |
CN108864396A (zh) * | 2018-07-24 | 2018-11-23 | 长虹美菱股份有限公司 | 一种冰箱聚氨酯硬泡发泡配方及其制备方法 |
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US4390645A (en) | 1979-11-23 | 1983-06-28 | The Dow Chemical Company | Stable dispersions of polymers in polyfunctional compounds having a plurality of active hydrogens and polyurethanes therefrom |
US4664563A (en) * | 1984-09-21 | 1987-05-12 | Basf Corporation | Rigid polyurethane foams with constant or slightly decreasing strain with an increasing stress in compression |
US5114988A (en) * | 1989-10-23 | 1992-05-19 | Basf Corporation | Polyether polyols having reduced unsaturation and polyurethane foams prepared therefrom |
JPH08193118A (ja) * | 1995-01-13 | 1996-07-30 | Takeda Chem Ind Ltd | 硬質ポリウレタンフォームおよびその製造方法 |
JPH09316482A (ja) * | 1996-05-31 | 1997-12-09 | Daido Kagaku Kogyo Kk | 水溶性切削研削油剤 |
US6979477B2 (en) | 2000-09-06 | 2005-12-27 | Urethane Soy Systems Company | Vegetable oil-based coating and method for application |
US7063877B2 (en) | 1998-09-17 | 2006-06-20 | Urethane Soy Systems Company, Inc. | Bio-based carpet material |
US6962636B2 (en) | 1998-09-17 | 2005-11-08 | Urethane Soy Systems Company, Inc. | Method of producing a bio-based carpet material |
CN1288185C (zh) | 2000-02-10 | 2006-12-06 | 陶氏环球技术公司 | 使用自动催化多羟基化合物制备的低挥发聚氨酯聚合物 |
BR0208765A (pt) | 2001-04-01 | 2005-01-04 | Dow Global Technologies Inc | Espuma de poliuretano rìgidas |
EP1369443B1 (en) * | 2002-06-04 | 2007-04-04 | Mitsubishi Gas Chemical Company, Inc. | Gas-barrier polyurethane resin, and adhesive for laminate, film and paint containing the same |
US7960444B2 (en) | 2003-04-25 | 2011-06-14 | Dow Global Technologies Llc | Vegetable oil based polyols and polyurethanes made therefrom |
DE602004002403T2 (de) | 2003-04-25 | 2007-04-05 | Dow Global Technologies, Inc., Midland | Aus hydroxymethylgruppenhaltigen polyesterpolyolen hergestellte polyurethanschaumstoffe |
DE10324306A1 (de) * | 2003-05-30 | 2004-12-16 | Bayer Materialscience Ag | Wässrige PUR-Dispersionen zur Herstellung von Beschichtungen mit Softfeel-Effekt |
DE102004048728A1 (de) * | 2004-10-05 | 2006-04-06 | Basf Ag | Verfahren zur Herstellung von Polyurethan-Hartschaumstoffen |
BRPI0610831B1 (pt) | 2005-04-25 | 2018-04-10 | Cargill, Incorporated | Espumas de poliuretano compreendendo polióis oligoméricos e métodos de fabricar artigo de espuma moldada de poliuretano e artigo de espuma de poliuretano slabstock |
WO2007019051A1 (en) | 2005-08-03 | 2007-02-15 | Dow Global Technologies, Inc. | Polyurethanes made from hydroxyl-containing esters of fatty acids |
WO2007019063A1 (en) | 2005-08-03 | 2007-02-15 | Dow Global Technologies, Inc. | Polyurethanes made from hydroxyl-containing fatty acid amides |
AU2006315842A1 (en) | 2005-11-14 | 2007-05-24 | Dow Global Technologies Llc | Method of molding rigid polyurethane foams with enhanced thermal conductivity |
WO2008094238A1 (en) * | 2007-01-30 | 2008-08-07 | Dow Global Technologies, Inc. | Ortho-cyclohexanediamine-initiated polyols and rigid polyurethane foam made therefrom |
ES2792351T3 (es) * | 2008-06-10 | 2020-11-11 | Dow Global Technologies Llc | Polioles iniciados con 1,3- o 1,4-bis(aminometil)ciclohexano y espuma de poliuretano rígida obtenida a partir de ellos |
ES2378504T3 (es) * | 2008-06-10 | 2012-04-13 | Dow Global Technologies Inc. | Procedimiento para preparar una espuma rígida de poliuretano a partir de polioles iniciados con metilenbis(ciclohexilamina) |
US20110130477A1 (en) * | 2008-07-30 | 2011-06-02 | Birch Adrian J | Rigid polyurethane foam systems based on ortho-cyclohexanediamine-initiated polyols |
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2010
- 2010-09-21 CN CN2010800526977A patent/CN102666627B/zh active Active
- 2010-09-21 MX MX2012003741A patent/MX2012003741A/es active IP Right Grant
- 2010-09-21 KR KR1020127010972A patent/KR101837207B1/ko active IP Right Grant
- 2010-09-21 ES ES10761090.9T patent/ES2447292T3/es active Active
- 2010-09-21 EP EP10761090.9A patent/EP2483325B1/en active Active
- 2010-09-21 BR BR112012006812-1A patent/BR112012006812A2/pt not_active Application Discontinuation
- 2010-09-21 JP JP2012532129A patent/JP5933442B2/ja active Active
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CN102666627B (zh) | 2013-12-18 |
EP2483325B1 (en) | 2013-12-04 |
US20120172470A1 (en) | 2012-07-05 |
MX2012003741A (es) | 2012-04-30 |
KR101837207B1 (ko) | 2018-03-09 |
JP2013506045A (ja) | 2013-02-21 |
CN102666627A (zh) | 2012-09-12 |
BR112012006812A2 (pt) | 2020-08-18 |
ES2447292T3 (es) | 2014-03-11 |
WO2011041163A1 (en) | 2011-04-07 |
KR20120105436A (ko) | 2012-09-25 |
EP2483325A1 (en) | 2012-08-08 |
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