JP5670614B2 - 触媒組成物及びその使用方法 - Google Patents
触媒組成物及びその使用方法 Download PDFInfo
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- JP5670614B2 JP5670614B2 JP2008516897A JP2008516897A JP5670614B2 JP 5670614 B2 JP5670614 B2 JP 5670614B2 JP 2008516897 A JP2008516897 A JP 2008516897A JP 2008516897 A JP2008516897 A JP 2008516897A JP 5670614 B2 JP5670614 B2 JP 5670614B2
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- 239000000203 mixture Substances 0.000 title claims description 106
- 239000003054 catalyst Substances 0.000 title claims description 78
- 238000000034 method Methods 0.000 title description 19
- -1 alkali metal carboxylates Chemical class 0.000 claims description 70
- 239000002904 solvent Substances 0.000 claims description 44
- 239000005056 polyisocyanate Substances 0.000 claims description 33
- 229920001228 polyisocyanate Polymers 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 239000012948 isocyanate Substances 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 26
- 150000002513 isocyanates Chemical class 0.000 claims description 25
- 229910052783 alkali metal Inorganic materials 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 150000007942 carboxylates Chemical class 0.000 claims description 17
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 16
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 14
- 229920000582 polyisocyanurate Polymers 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 12
- 239000011495 polyisocyanurate Substances 0.000 claims description 12
- 229910019142 PO4 Inorganic materials 0.000 claims description 11
- 229920005862 polyol Polymers 0.000 claims description 11
- 150000003077 polyols Chemical class 0.000 claims description 11
- 229920002635 polyurethane Polymers 0.000 claims description 11
- 239000004814 polyurethane Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000010452 phosphate Substances 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 125000000524 functional group Chemical group 0.000 claims description 9
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 8
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000000010 aprotic solvent Substances 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 claims description 4
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 4
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical group COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- 235000011054 acetic acid Nutrition 0.000 claims description 4
- 239000001361 adipic acid Substances 0.000 claims description 4
- 235000011037 adipic acid Nutrition 0.000 claims description 4
- 125000005600 alkyl phosphonate group Chemical group 0.000 claims description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 239000001530 fumaric acid Substances 0.000 claims description 4
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- OFXSXYCSPVKZPF-UHFFFAOYSA-N methoxyperoxymethane Chemical compound COOOC OFXSXYCSPVKZPF-UHFFFAOYSA-N 0.000 claims description 4
- 150000005677 organic carbonates Chemical class 0.000 claims description 4
- 235000006408 oxalic acid Nutrition 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 235000019260 propionic acid Nutrition 0.000 claims description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 4
- 150000003462 sulfoxides Chemical class 0.000 claims description 4
- 229940005605 valeric acid Drugs 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- AATNZNJRDOVKDD-UHFFFAOYSA-N 1-[ethoxy(ethyl)phosphoryl]oxyethane Chemical group CCOP(=O)(CC)OCC AATNZNJRDOVKDD-UHFFFAOYSA-N 0.000 claims description 2
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- NDWWLJQHOLSEHX-UHFFFAOYSA-L calcium;octanoate Chemical compound [Ca+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O NDWWLJQHOLSEHX-UHFFFAOYSA-L 0.000 claims description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- BTAUEIDLAAYHSL-UHFFFAOYSA-M lithium;octanoate Chemical group [Li+].CCCCCCCC([O-])=O BTAUEIDLAAYHSL-UHFFFAOYSA-M 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- PHZLMBHDXVLRIX-UHFFFAOYSA-M potassium lactate Chemical compound [K+].CC(O)C([O-])=O PHZLMBHDXVLRIX-UHFFFAOYSA-M 0.000 claims description 2
- 239000001521 potassium lactate Substances 0.000 claims description 2
- 235000011085 potassium lactate Nutrition 0.000 claims description 2
- 229960001304 potassium lactate Drugs 0.000 claims description 2
- VAKMIIPDYZXBEV-DPMBMXLASA-M potassium;(z,12r)-12-hydroxyoctadec-9-enoate Chemical compound [K+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O VAKMIIPDYZXBEV-DPMBMXLASA-M 0.000 claims description 2
- VUDCQRVTUKBZGG-UHFFFAOYSA-M potassium;3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate Chemical compound [K+].OCC(C)(CO)C([O-])=O VUDCQRVTUKBZGG-UHFFFAOYSA-M 0.000 claims description 2
- RLEFZEWKMQQZOA-UHFFFAOYSA-M potassium;octanoate Chemical compound [K+].CCCCCCCC([O-])=O RLEFZEWKMQQZOA-UHFFFAOYSA-M 0.000 claims description 2
- 229960005480 sodium caprylate Drugs 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- BYKRNSHANADUFY-UHFFFAOYSA-M sodium octanoate Chemical compound [Na+].CCCCCCCC([O-])=O BYKRNSHANADUFY-UHFFFAOYSA-M 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 6
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims 3
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims 3
- 229940114077 acrylic acid Drugs 0.000 claims 3
- 239000004310 lactic acid Substances 0.000 claims 3
- 235000014655 lactic acid Nutrition 0.000 claims 3
- 229960000448 lactic acid Drugs 0.000 claims 3
- 229960002446 octanoic acid Drugs 0.000 claims 3
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 claims 3
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims 3
- 229960003656 ricinoleic acid Drugs 0.000 claims 3
- 150000001734 carboxylic acid salts Chemical class 0.000 claims 2
- 238000009472 formulation Methods 0.000 claims 2
- 241000255925 Diptera Species 0.000 claims 1
- 229920005830 Polyurethane Foam Polymers 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- NXHXNTAEDQTBLD-UHFFFAOYSA-N n,n-dimethyl-3-(triazinan-1-yl)propan-1-amine Chemical compound CN(C)CCCN1CCCNN1 NXHXNTAEDQTBLD-UHFFFAOYSA-N 0.000 claims 1
- 239000011496 polyurethane foam Substances 0.000 claims 1
- 150000004072 triols Chemical class 0.000 claims 1
- 239000006260 foam Substances 0.000 description 46
- 239000000243 solution Substances 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 11
- 239000004604 Blowing Agent Substances 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 239000003063 flame retardant Substances 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 229920000570 polyether Polymers 0.000 description 6
- 229920006389 polyphenyl polymer Polymers 0.000 description 6
- 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 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 5
- 238000005755 formation reaction Methods 0.000 description 5
- 229920000515 polycarbonate Polymers 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical group CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 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 4
- 239000004114 Ammonium polyphosphate Chemical class 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004970 Chain extender Substances 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 235000019826 ammonium polyphosphate Nutrition 0.000 description 3
- 229920001276 ammonium polyphosphate Chemical class 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000011256 inorganic filler Substances 0.000 description 3
- 239000012766 organic filler Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 3
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 2
- 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
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RDOFJDLLWVCMRU-UHFFFAOYSA-N Diisobutyl adipate Chemical compound CC(C)COC(=O)CCCCC(=O)OCC(C)C RDOFJDLLWVCMRU-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-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
- 125000002723 alicyclic group Chemical group 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical class O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- XLIDPNGFCHXNGX-UHFFFAOYSA-N dialuminum;oxygen(2-);silicon(4+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Al+3].[Al+3].[Si+4] XLIDPNGFCHXNGX-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004872 foam stabilizing agent Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
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- C08G18/092—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture oligomerisation to isocyanurate groups
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Description
a)1つ以上のポリイソシアネートと、
b)イソシアネート反応性水素原子を2つ以上有する1つ以上の化合物とを、
c)アルカリ金属カルボン酸塩及びアルカリ土類金属カルボン酸塩からなる群から選択される1つ以上の材料を含有し、ポリイソシアネート中のイソシアネート基、及び
d)発泡剤
と反応しない溶媒を含有する溶液を含んでなる触媒組成物の存在下で反応させることにより得られる。本発明の他の実施態様では、当該カルボン酸塩は触媒組成物に対して90重量%未満で量に存在する。本発明の更に別の実施態様では、水は触媒組成物に対して約25重量%未満の量で存在させてもよい。更に、他の公知の助剤及び添加剤を、剛性フォームの生産において使用してもよい。発泡剤は水、炭化水素、ガス、塩化フッ化炭化水素、ヒドロフルオロカーボン又はそれらのいかなる組み合わせであってもよい。この反応は、約150超のインデックスで実施してもよい。本発明の他の実施態様では、当該インデックスは約170〜約400の範囲である。任意に、2つ以上のイソシアネート反応性水素原子を有し、約32〜約399の分子量を有する鎖伸長剤及び/又は架橋剤を触媒組成物に存在させてもよい。本発明の更に別の実施態様では、当該2つ以上のイソシアネート反応性水素原子を有する1つ以上の化合物は約400〜約10,000の分子量を有してもよい。
比較実施例1及び2はそれぞれ、Pelron社及びAir Products及びChemical社から市販されている触媒組成物である。
これらの調製例は剛性フォームの調製に関する。剛性フォームの調製に使用した具体的な触媒組成物、材料及び添加量、並びにフォームの試験結果を下記の表2に列記する。
均質な混合物が得られるまで、イソシアネート以外の全ての調製物成分を容器中で撹拌した。次いでイソシアネートを均質となった混合物に添加し、プロペラを用いて5000rpmで7秒間撹拌した。反応混合物を直ちに木箱(20×20×20cm)に注入し、そこでフォームを膨張及び硬化させた。フォーム特性を24時間後に測定した。
異なる芳香族ポリエステルポリオール、発泡剤、及び場合によっては異なる触媒組成物を用いたことを除き、上記と同様の方法、並びに比較調製例11及び調製例12〜18に関して上記で用いた反応物質を用いて一連のフォームを調製した。比較調製例19及び20、並びに調製例21〜26のフォームの調製に使用した具体的な触媒組成物、材料及び添加量、並びにフォームの試験結果を下記の表3に列記する。
Claims (21)
- アルカリ金属カルボン酸塩及びアルカリ土類金属カルボン酸塩からなる群から選択される1つ以上の材料を、ポリイソシアネートの中のイソシアネート基と反応しない溶媒中に含んでなり、
前記金属カルボン酸塩が、ギ酸、酢酸、プロピオン酸、3−クロロプロピオン酸、ピバル酸、酪酸、γ−アミノ酪酸、吉草酸、アクリル酸、乳酸、リシノール酸、ジメチロールプロピオン酸、カプリル酸、2−エチルヘキサン酸、シュウ酸、マロン酸、コハク酸、グルタル酸、アジピン酸、マレイン酸、及びフマル酸からなる群より選択される少なくとも一種のカルボン酸に由来するものであり、
前記溶媒が、遊離ヒドロキシル基を有さないエーテル、メトキシエーテル、エステル、リン酸エステル、ジアルキルスルホキシド、アリール又はアルキルホスホネート、トリアルキルホスフェート、有機カーボネート、第三級アミン、ケトン及びそれらの組み合わせからなる群より選択される非プロトン溶媒である触媒組成物。 - 前記カルボン酸塩が炭酸ナトリウム、炭酸カリウム又は炭酸カルシウムからなる群から選択される、請求項1記載の組成物。
- 前記カルボン酸が1つ以上のカルボキシル基を含んでなり、46〜2000の分子量を有する、請求項1記載の組成物。
- 前記カルボン酸塩が1つ以上の水酸基を有するカルボン酸若しくはポリカルボン酸に由来する、請求項1記載の組成物。
- 前記カルボン酸塩が乳酸カリウム、リシノール酸カリウム及びジメチロールプロピオン酸カリウムからなる群から選択される、請求項4記載の組成物。
- 前記カルボン酸塩がカプリル酸リチウム、カプリル酸ナトリウム、カプリル酸カリウム、カプリル酸カルシウム、2−エチルヘキサン酸リチウム、2−エチルヘキサン酸ナトリウム、2−エチルヘキサン酸カルシウム又は2−エチルヘキサン酸カリウムである、請求項1記載の組成物。
- 前記溶媒が化学反応中にイソシアネート基と反応しない官能基を有する、請求項1記載の組成物。
- 前記溶媒がジ−エチル−エチル−ホスホネート、テトラメチレンスルホン、1−メチル−2−ピロリジノン、トリエチルホスフェート、トリブチルエチルホスフェート、アセトニトリル、ジメチルカーボネート、ジメチルベジルアミン、ジメチルアミノプロピルヘキサヒドロトリアジン、ペンタメチルジエチルエナミン、ジイソブチルケトン、メチルn−アミルケトン及びそれらの組み合わせからなる群から選択される非プロトン溶媒である、請求項1記載の触媒組成物。
- 前記溶媒が遊離ヒドロキシル基を有さないエーテルである、請求項1記載の組成物。
- 前記溶媒が、モノオール、ジオール、トリオール又はグリコールエーテルとモノ−、ジ−又はポリカルボン酸とに由来する遊離ヒドロキシル基を有さないエステル、グリセロールと脂肪族酸若しくは芳香族酸とに由来するトリグリセリド、脂肪族若しくは芳香族のカルボン酸とアミドとに由来する遊離−NH基を有さないアミン、又はそれらの組み合わせである、請求項1記載の組成物。
- 前記溶媒が組成物に対して90重量%未満の量で存在する、請求項1記載の組成物。
- 前記カルボン酸塩が溶液の合計量に対して10重量%〜90重量%の量で存在する、請求項11記載の組成物。
- 前記溶媒が溶液の合計量に対して10重量%〜90重量%の量で存在する、請求項11記載の組成物。
- 水が組成物に対して25重量%未満の量で存在する、請求項1記載の組成物。
- 組成物中に存在する水の量が、組成物の最終的な重量に対して5重量%未満である、請求項14記載の組成物。
- 前記組成物がイソシアネートプレポリマー、イソシアネートプレポリマー又はポリオール成分に添加される、請求項1記載の組成物。
- 20未満のOH値(mg(KOH)/g(触媒組成物))を有する、請求項1記載の組成物。
- アルカリ金属カルボン酸塩及びアルカリ土類金属カルボン酸塩からなる群から選択される1つ以上の材料を溶媒中に含有する溶液を含んでなる触媒組成物であって、当該溶媒がポリイソシアネート中のイソシアネート基、及び当該触媒組成物に対して25重量%未満の量で存在する水と反応せず、当該溶媒が触媒組成物に対して90重量%未満の量で存在し、
前記金属カルボン酸塩が、ギ酸、酢酸、プロピオン酸、3−クロロプロピオン酸、ピバル酸、酪酸、γ−アミノ酪酸、吉草酸、アクリル酸、乳酸、リシノール酸、ジメチロールプロピオン酸、カプリル酸、2−エチルヘキサン酸、シュウ酸、マロン酸、コハク酸、グルタル酸、アジピン酸、マレイン酸、及びフマル酸からなる群より選択される少なくとも一種のカルボン酸に由来するものであり、
前記溶媒が、遊離ヒドロキシル基を有さないエーテル、メトキシエーテル、エステル、リン酸エステル、ジアルキルスルホキシド、アリール又はアルキルホスホネート、トリアルキルホスフェート、有機カーボネート、第三級アミン、ケトン及びそれらの組み合わせからなる群より選択される非プロトン溶媒である触媒組成物。 - ポリウレタン又はポリイソシアヌレート調製物の合計量に対して0.3重量%〜10%の量の請求項18記載の組成物が用いられている、前記ポリウレタン又はポリイソシアヌレート調製物。
- ポリウレタン又はポリイソシアヌレート調製物の合計量に対して0.3重量%〜10%の量の請求項1記載の組成物が用いられている、前記ポリウレタン又はポリイソシアヌレート調製物。
- 1つ以上のポリイソシアネートと、イソシアネート反応性水素原子を2つ以上有する1つ以上の化合物とを、アルカリ金属カルボン酸塩及びアルカリ土類金属カルボン酸塩からなる群から選択される1つ以上の材料を含有し、ポリイソシアネート中のイソシアネート基と反応しない溶媒を含んでなる触媒組成物の存在下で反応させることにより得られるウレタン基及びイソシアヌレート基を含んでなり、
前記金属カルボン酸塩が、ギ酸、酢酸、プロピオン酸、3−クロロプロピオン酸、ピバル酸、酪酸、γ−アミノ酪酸、吉草酸、アクリル酸、乳酸、リシノール酸、ジメチロールプロピオン酸、カプリル酸、2−エチルヘキサン酸、シュウ酸、マロン酸、コハク酸、グルタル酸、アジピン酸、マレイン酸、及びフマル酸からなる群より選択される少なくとも一種のカルボン酸に由来するものであり、
前記溶媒が、遊離ヒドロキシル基を有さないエーテル、メトキシエーテル、エステル、リン酸エステル、ジアルキルスルホキシド、アリール又はアルキルホスホネート、トリアルキルホスフェート、有機カーボネート、第三級アミン、ケトン及びそれらの組み合わせからなる群より選択される非プロトン溶媒であるポリウレタンフォーム。
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JP4104539B2 (ja) * | 2003-04-22 | 2008-06-18 | 花王株式会社 | ポリイソシアヌレートフォームの製造法 |
US20040249078A1 (en) * | 2003-06-04 | 2004-12-09 | Honeywell International, Inc. | Foam catalyst systems |
US8729146B2 (en) | 2005-06-14 | 2014-05-20 | Momentive Performance Materials Inc. | Catalyst composition and process using same |
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Also Published As
Publication number | Publication date |
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MX2007015708A (es) | 2008-04-15 |
UA92176C2 (ru) | 2010-10-11 |
TW200712079A (en) | 2007-04-01 |
CA2611739A1 (en) | 2006-12-28 |
EP1913048B1 (en) | 2019-11-06 |
WO2006138050A1 (en) | 2006-12-28 |
US20060281827A1 (en) | 2006-12-14 |
JP2008544041A (ja) | 2008-12-04 |
CN101248100A (zh) | 2008-08-20 |
BRPI0611854A2 (pt) | 2010-10-13 |
US20140171295A1 (en) | 2014-06-19 |
KR101392735B1 (ko) | 2014-05-14 |
ZA200800346B (en) | 2009-04-29 |
CA2611739C (en) | 2015-12-08 |
BRPI0611854B1 (pt) | 2019-05-14 |
EP1913048A1 (en) | 2008-04-23 |
KR20080026173A (ko) | 2008-03-24 |
CN101248100B (zh) | 2012-10-03 |
AU2006259810A1 (en) | 2006-12-28 |
RU2008101421A (ru) | 2009-07-20 |
US8729146B2 (en) | 2014-05-20 |
TWI508985B (zh) | 2015-11-21 |
ES2764770T3 (es) | 2020-06-04 |
PL1913048T3 (pl) | 2020-05-18 |
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