JP2013530270A5 - - Google Patents
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- JP2013530270A5 JP2013530270A5 JP2013511617A JP2013511617A JP2013530270A5 JP 2013530270 A5 JP2013530270 A5 JP 2013530270A5 JP 2013511617 A JP2013511617 A JP 2013511617A JP 2013511617 A JP2013511617 A JP 2013511617A JP 2013530270 A5 JP2013530270 A5 JP 2013530270A5
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- JP
- Japan
- Prior art keywords
- mol
- acid
- alcohol
- carbon atoms
- reaction
- 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.)
- Granted
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- 230000002209 hydrophobic effect Effects 0.000 claims description 81
- 125000004432 carbon atom Chemical group C* 0.000 claims description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 65
- 239000000203 mixture Substances 0.000 claims description 61
- 238000006243 chemical reaction Methods 0.000 claims description 60
- 239000003921 oil Substances 0.000 claims description 59
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 58
- 239000004417 polycarbonate Substances 0.000 claims description 48
- 229920000515 polycarbonate Polymers 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 47
- 229920005830 Polyurethane Foam Polymers 0.000 claims description 46
- -1 aliphatic dicarboxylic acids Chemical class 0.000 claims description 46
- 239000011496 polyurethane foam Substances 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 45
- 239000002253 acid Substances 0.000 claims description 43
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 42
- 229920005862 polyol Polymers 0.000 claims description 40
- 150000003077 polyols Chemical class 0.000 claims description 40
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 39
- 150000001298 alcohols Chemical class 0.000 claims description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 36
- 229920000728 polyester Polymers 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 25
- 150000002009 diols Chemical class 0.000 claims description 21
- 125000001931 aliphatic group Chemical group 0.000 claims description 20
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 20
- 239000004970 Chain extender Substances 0.000 claims description 18
- 229920005906 polyester polyol Polymers 0.000 claims description 16
- 239000005056 polyisocyanate Substances 0.000 claims description 16
- 229920001228 polyisocyanate Polymers 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 13
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 10
- 239000004604 Blowing Agent Substances 0.000 claims description 9
- 238000010521 absorption reaction Methods 0.000 claims description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 9
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 9
- 239000007858 starting material Substances 0.000 claims description 9
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 230000001588 bifunctional effect Effects 0.000 claims description 4
- 229920006150 hyperbranched polyester Polymers 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 239000010779 crude oil Substances 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 1
- 230000007123 defense Effects 0.000 claims 1
- 230000009257 reactivity Effects 0.000 claims 1
- 235000019198 oils Nutrition 0.000 description 54
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 39
- 239000006260 foam Substances 0.000 description 37
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 29
- 125000000524 functional group Chemical group 0.000 description 21
- 238000004519 manufacturing process Methods 0.000 description 21
- 239000000463 material Substances 0.000 description 20
- 210000004027 cell Anatomy 0.000 description 19
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 16
- 239000000194 fatty acid Substances 0.000 description 15
- 150000002605 large molecules Chemical class 0.000 description 15
- 239000007788 liquid Substances 0.000 description 15
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 14
- 229920002635 polyurethane Polymers 0.000 description 14
- 239000004814 polyurethane Substances 0.000 description 14
- 235000014113 dietary fatty acids Nutrition 0.000 description 13
- 229930195729 fatty acid Natural products 0.000 description 13
- 239000004721 Polyphenylene oxide Substances 0.000 description 12
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 12
- 150000004665 fatty acids Chemical class 0.000 description 12
- 229920000570 polyether Polymers 0.000 description 12
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 10
- 239000004926 polymethyl methacrylate Substances 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 239000012948 isocyanate Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 7
- 239000001361 adipic acid Substances 0.000 description 7
- 235000011037 adipic acid Nutrition 0.000 description 7
- 125000005587 carbonate group Chemical group 0.000 description 7
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 7
- 150000002513 isocyanates Chemical class 0.000 description 7
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 7
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 6
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 6
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- 239000005642 Oleic acid Substances 0.000 description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000004088 foaming agent Substances 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000001179 sorption measurement Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 125000001165 hydrophobic group Chemical group 0.000 description 5
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 5
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 238000000197 pyrolysis Methods 0.000 description 5
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 5
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 238000006068 polycondensation reaction Methods 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 229960004063 propylene glycol Drugs 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 4
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- 229940043375 1,5-pentanediol Drugs 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 229930006000 Sucrose Natural products 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000000412 dendrimer Substances 0.000 description 3
- 229920000736 dendritic polymer Polymers 0.000 description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- AVIYEYCFMVPYST-UHFFFAOYSA-N hexane-1,3-diol Chemical compound CCCC(O)CCO AVIYEYCFMVPYST-UHFFFAOYSA-N 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000011256 inorganic filler Substances 0.000 description 3
- 229910003475 inorganic filler Inorganic materials 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 230000035882 stress Effects 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 150000003628 tricarboxylic acids Chemical class 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- 150000004072 triols Chemical class 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 2
- 229940031723 1,2-octanediol Drugs 0.000 description 2
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 2
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| EP10164188.4 | 2010-05-27 | ||
| PCT/EP2011/058051 WO2011147724A1 (de) | 2010-05-27 | 2011-05-18 | Ölaufnehmende polyurethanschwämme mit guten mechanischen eigenschaften |
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| US8987357B2 (en) | 2011-05-27 | 2015-03-24 | Basf Se | Thermoplastic molding composition |
| CN105658697B (zh) * | 2013-09-20 | 2017-09-19 | 三菱瓦斯化学株式会社 | 能够用作油吸附材料的聚碳酸酯树脂 |
| KR101645117B1 (ko) * | 2015-01-02 | 2016-08-12 | 한국가스공사 | 경질 우레탄 폼 제조용 조성물 및 이의 제조 방법 |
| US10751695B2 (en) | 2015-02-26 | 2020-08-25 | Test 1 S.R.L. | Absorbent element, assembly and fabrication process |
| CN105131233B (zh) * | 2015-07-21 | 2017-10-10 | 浙江川洋家居股份有限公司 | 一种聚酯改性海绵及其制备方法 |
| CN106925238B (zh) * | 2017-04-10 | 2019-04-09 | 福州大学 | 一种海绵负载型有机溶剂吸收剂及其制备方法 |
| CN108727193B (zh) * | 2017-04-24 | 2021-03-16 | 中国石油化工股份有限公司 | 碳酸二苯酯类化合物的制备方法 |
| CN107892759A (zh) * | 2017-10-19 | 2018-04-10 | 苏州无为环境科技有限公司 | 一种脂肪酸修饰的超疏水聚氨酯泡沫吸油材料的制备方法 |
| CN108587122A (zh) * | 2018-03-23 | 2018-09-28 | 长沙小新新能源科技有限公司 | 一种高吸油高回弹海绵及其制备方法 |
| CN113308899B (zh) * | 2021-05-26 | 2022-05-06 | 东华大学 | 一种表面上浆后的碳纤维及其制备方法和应用 |
| KR102841094B1 (ko) * | 2022-11-11 | 2025-07-31 | 한국과학기술연구원 | 유흡착재 |
| CN116042129B (zh) * | 2022-12-15 | 2023-12-26 | 上海兰庆新材料技术股份有限公司 | 一种丙烯酸酯基uv光固化保护膜及其制备方法 |
| CN118206800B (zh) * | 2024-04-17 | 2024-10-18 | 扬州三江环安设备有限公司 | 一种吸油性聚氨酯泡沫材料及其制备方法 |
| KR102776718B1 (ko) | 2024-06-27 | 2025-03-06 | 문기배 | 실리카겔을 이용한 친환경적인 스펀지의 제조방법 |
| KR102776714B1 (ko) | 2024-06-27 | 2025-03-06 | 문기배 | 친환경적인 스펀지의 제조방법 |
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| DE111394C (enExample) | ||||
| US3523093A (en) | 1961-11-28 | 1970-08-04 | Paul Stamberger | Method of producing polyurethanes by reacting polyisocyanate with a preformed polymer resulting from polymerization of ethylenically unsaturated monomers |
| US3304273A (en) | 1963-02-06 | 1967-02-14 | Stamberger Paul | Method of preparing polyurethanes from liquid, stable, reactive, filmforming polymer/polyol mixtures formed by polymerizing an ethylenically unsaturated monomer in a polyol |
| GB1022434A (en) | 1961-11-28 | 1966-03-16 | Union Carbide Corp | Improvements in and relating to polymers |
| DE1152536B (de) | 1962-03-30 | 1963-08-08 | Bayer Ag | Verfahren zur Herstellung Urethangruppen enthaltender Schaumstoffe |
| DE1152537B (de) | 1962-06-02 | 1963-08-08 | Bayer Ag | Verfahren zur Herstellung von homogenen, Urethangruppen aufweisenden Kunststoffen |
| DE2738268A1 (de) | 1977-08-25 | 1979-03-08 | Basf Ag | Hydrophobe polyurethanschaumstoffe zur oelabsorption |
| DE3405875A1 (de) | 1984-02-18 | 1985-08-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von zelligen oder kompakten polyurethan-polyharnstoff-formkoerpern mit verbesserten entformungseigenschaften sowie innere formtrennmittel fuer das polyisocyanat-polyadditionsverfahren |
| DE3607447A1 (de) | 1986-03-07 | 1987-09-10 | Basf Ag | Verfahren zur herstellung von formkoerpern mit einem zelligen kern und einer verdichteten randzone mit verbesserten entformungseigenschaften |
| ES8800697A1 (es) | 1986-06-10 | 1987-12-01 | Hoocker Sa | Procedimiento para la obtencion de dispersiones de polimeros en poliesteres hidroxilados. |
| DE3631842A1 (de) | 1986-09-19 | 1988-03-24 | Basf Ag | Innere formtrennmittel, deren verwendung zur herstellung von formkoerpern nach dem polyisocyanat-polyadditionsverfahren und verfahren zur herstellung der formkoerper |
| CN100381479C (zh) | 2003-09-12 | 2008-04-16 | 巴斯福股份公司 | 高官能度高度支化或超支化聚碳酸酯、其制备及用途 |
| US20080203031A1 (en) | 2004-02-03 | 2008-08-28 | Timothy Thomson | Foam Composite for Absorption of Hydrocarbon and Process for Making Same |
| DE102004017294A1 (de) | 2004-04-05 | 2005-10-20 | Basf Ag | Verfahren zur Herstellung von Polyurethan-Schaumstoffen |
| WO2005098763A2 (de) | 2004-04-06 | 2005-10-20 | Giesecke & Devrient Gmbh | Vorrichtung und verfahren zur bearbeitung von banknoten |
| JP4526036B2 (ja) | 2006-08-17 | 2010-08-18 | 株式会社タイトー | カードゲーム装置用のカードテーブル及びそのカードテーブルを具備したカードゲーム装置 |
| EP1911781A1 (en) * | 2006-10-12 | 2008-04-16 | Arizona Chemical Company | Oil absorbing foam |
| ES2359855T3 (es) | 2006-12-11 | 2011-05-27 | Basf Se | Espumas blandas de poliuretano de alta elasticidad. |
| WO2009112576A1 (de) | 2008-03-14 | 2009-09-17 | Basf Se | Grobzellige polyurethanelastomere |
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2010
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- 2011-05-18 MX MX2012013514A patent/MX2012013514A/es active IP Right Grant
- 2011-05-18 MY MYPI2012005050A patent/MY160512A/en unknown
- 2011-05-18 JP JP2013511617A patent/JP6338372B2/ja not_active Expired - Fee Related
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- 2011-05-18 CA CA2799130A patent/CA2799130C/en not_active Expired - Fee Related
- 2011-05-18 KR KR1020127033446A patent/KR101844092B1/ko not_active Expired - Fee Related
- 2011-05-18 CN CN201180026154.2A patent/CN102906145B/zh active Active
- 2011-05-18 AU AU2011257432A patent/AU2011257432B2/en not_active Ceased
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