JP6641285B2 - ポリウレタン材料における使用のためのピロリジンに基づく触媒 - Google Patents
ポリウレタン材料における使用のためのピロリジンに基づく触媒 Download PDFInfo
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- JP6641285B2 JP6641285B2 JP2016554605A JP2016554605A JP6641285B2 JP 6641285 B2 JP6641285 B2 JP 6641285B2 JP 2016554605 A JP2016554605 A JP 2016554605A JP 2016554605 A JP2016554605 A JP 2016554605A JP 6641285 B2 JP6641285 B2 JP 6641285B2
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- Prior art keywords
- catalyst
- pyrrolidine
- polyurethane
- bis
- foam
- 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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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title claims description 138
- 239000003054 catalyst Substances 0.000 title claims description 124
- 229920002635 polyurethane Polymers 0.000 title claims description 45
- 239000004814 polyurethane Substances 0.000 title claims description 45
- 239000000463 material Substances 0.000 title claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 50
- 229920005862 polyol Polymers 0.000 claims description 48
- -1 pyrrolidinylmethyl butyl morpholine Chemical compound 0.000 claims description 45
- 239000006260 foam Substances 0.000 claims description 42
- 150000003077 polyols Chemical class 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 37
- 150000001412 amines Chemical class 0.000 claims description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 22
- 239000005056 polyisocyanate Substances 0.000 claims description 21
- 229920001228 polyisocyanate Polymers 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 13
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 12
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- 238000005187 foaming Methods 0.000 claims description 9
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 8
- 239000003063 flame retardant Substances 0.000 claims description 7
- 239000012948 isocyanate Substances 0.000 claims description 7
- 150000002513 isocyanates Chemical class 0.000 claims description 7
- 239000004094 surface-active agent Substances 0.000 claims description 7
- SYHAYUSMVWWPKJ-UHFFFAOYSA-N 1-[2-(2-pyrrolidin-1-ylethoxy)ethyl]pyrrolidine Chemical compound C1CCCN1CCOCCN1CCCC1 SYHAYUSMVWWPKJ-UHFFFAOYSA-N 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 229920001971 elastomer Polymers 0.000 claims description 6
- 239000000806 elastomer Substances 0.000 claims description 6
- ZMSQJSMSLXVTKN-UHFFFAOYSA-N 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine Chemical compound C1COCCN1CCOCCN1CCOCC1 ZMSQJSMSLXVTKN-UHFFFAOYSA-N 0.000 claims description 5
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 239000004615 ingredient Substances 0.000 claims description 5
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical class CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 claims description 4
- ZMJQROKRSPSLFH-UHFFFAOYSA-N 3-pyrrolidin-1-ylpropan-1-ol Chemical compound OCCCN1CCCC1 ZMJQROKRSPSLFH-UHFFFAOYSA-N 0.000 claims description 4
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 claims description 4
- 239000004970 Chain extender Substances 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 4
- 239000000049 pigment Substances 0.000 claims description 4
- 229920001281 polyalkylene Polymers 0.000 claims description 4
- 229920005906 polyester polyol Polymers 0.000 claims description 4
- 150000003512 tertiary amines Chemical group 0.000 claims description 4
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims description 3
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical group CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 claims description 3
- 229920000103 Expandable microsphere Polymers 0.000 claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 3
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 239000002131 composite material Substances 0.000 claims description 3
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 239000004872 foam stabilizing agent Substances 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 238000009413 insulation Methods 0.000 claims description 3
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 239000011493 spray foam Substances 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 claims description 3
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 2
- NIXYMFJMHHIQAC-UHFFFAOYSA-N 1,1-bis(dimethylamino)propan-2-ol Chemical compound CC(O)C(N(C)C)N(C)C NIXYMFJMHHIQAC-UHFFFAOYSA-N 0.000 claims description 2
- PNHGJPJOMCXSKN-UHFFFAOYSA-N 2-(1-methylpyrrolidin-2-yl)ethanamine Chemical compound CN1CCCC1CCN PNHGJPJOMCXSKN-UHFFFAOYSA-N 0.000 claims description 2
- YSAANLSYLSUVHB-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]ethanol Chemical compound CN(C)CCOCCO YSAANLSYLSUVHB-UHFFFAOYSA-N 0.000 claims description 2
- FZQMJOOSLXFQSU-UHFFFAOYSA-N 3-[3,5-bis[3-(dimethylamino)propyl]-1,3,5-triazinan-1-yl]-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCN1CN(CCCN(C)C)CN(CCCN(C)C)C1 FZQMJOOSLXFQSU-UHFFFAOYSA-N 0.000 claims description 2
- GVGWZCPKZOZRMX-UHFFFAOYSA-N 3-amino-6-(dimethylamino)-3-[3-(dimethylamino)propyl]hexan-2-ol Chemical compound CN(C)CCCC(N)(C(O)C)CCCN(C)C GVGWZCPKZOZRMX-UHFFFAOYSA-N 0.000 claims description 2
- 229940105325 3-dimethylaminopropylamine Drugs 0.000 claims description 2
- JAEQOSKUYPMJAT-UHFFFAOYSA-N 4-(2-methoxyethyl)morpholine Chemical compound COCCN1CCOCC1 JAEQOSKUYPMJAT-UHFFFAOYSA-N 0.000 claims description 2
- LMRKVKPRHROQRR-UHFFFAOYSA-N 4-butylmorpholine Chemical compound CCCCN1CCOCC1 LMRKVKPRHROQRR-UHFFFAOYSA-N 0.000 claims description 2
- KIZRVUBBJQEPIC-UHFFFAOYSA-N C(C)NC(=O)N.CN1CCCC1.CN1CCCC1 Chemical compound C(C)NC(=O)N.CN1CCCC1.CN1CCCC1 KIZRVUBBJQEPIC-UHFFFAOYSA-N 0.000 claims description 2
- IYPHCNPSJJJTLA-UHFFFAOYSA-N NC(=O)N.CN1CCNCC1.CN1CCNCC1 Chemical compound NC(=O)N.CN1CCNCC1.CN1CCNCC1 IYPHCNPSJJJTLA-UHFFFAOYSA-N 0.000 claims description 2
- 239000012963 UV stabilizer Substances 0.000 claims description 2
- 239000006096 absorbing agent Substances 0.000 claims description 2
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical class NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 239000002216 antistatic agent Substances 0.000 claims description 2
- 239000003139 biocide Substances 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 229960002887 deanol Drugs 0.000 claims description 2
- 229940043276 diisopropanolamine Drugs 0.000 claims description 2
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000009730 filament winding Methods 0.000 claims description 2
- 239000004088 foaming agent Substances 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 229940102253 isopropanolamine Drugs 0.000 claims description 2
- 230000014759 maintenance of location Effects 0.000 claims description 2
- 239000006082 mold release agent Substances 0.000 claims description 2
- BXYVQNNEFZOBOZ-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-n',n'-dimethylpropane-1,3-diamine Chemical compound CN(C)CCCNCCCN(C)C BXYVQNNEFZOBOZ-UHFFFAOYSA-N 0.000 claims description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 2
- 239000012744 reinforcing agent Substances 0.000 claims description 2
- 239000000565 sealant Substances 0.000 claims description 2
- 239000000779 smoke Substances 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
- OMDXZWUHIHTREC-UHFFFAOYSA-N 1-[2-(dimethylamino)ethoxy]ethanol Chemical compound CC(O)OCCN(C)C OMDXZWUHIHTREC-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- LSYBWANTZYUTGJ-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl-methylamino]ethanol Chemical compound CN(C)CCN(C)CCO LSYBWANTZYUTGJ-UHFFFAOYSA-N 0.000 claims 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 239000000417 fungicide Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 20
- 125000003545 alkoxy group Chemical group 0.000 description 19
- 229920005830 Polyurethane Foam Polymers 0.000 description 18
- 239000011496 polyurethane foam Substances 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 239000004604 Blowing Agent Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 125000004043 oxo group Chemical group O=* 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 8
- 239000004005 microsphere Substances 0.000 description 7
- 230000009257 reactivity Effects 0.000 description 7
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 229920002396 Polyurea Polymers 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000007664 blowing Methods 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 229920003086 cellulose ether Polymers 0.000 description 2
- 125000003636 chemical group Chemical group 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- CIXSDMKDSYXUMJ-UHFFFAOYSA-N n,n-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 description 2
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2203/00—Foams characterized by the expanding agent
- C08J2203/10—Water or water-releasing compounds
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- C08J2203/00—Foams characterized by the expanding agent
- C08J2203/14—Saturated hydrocarbons, e.g. butane; Unspecified hydrocarbons
- C08J2203/142—Halogenated saturated hydrocarbons, e.g. H3C-CF3
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- C08J2203/00—Foams characterized by the expanding agent
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Description
適用なし
適用なし
本開示は、軟質及び硬質ポリウレタンフォームならびに他のポリウレタン材料の製造における使用のためのピロリジンに基づく触媒を目的とする。
ポリウレタンフォームは広く知られており、自動車及び住宅産業におけるような多様な用途で用いられている。これらのフォームは種々の添加物の存在下におけるポリイソシアナートとポリオールの反応により製造される。1つのそのような添加物はアミン触媒であり、それは発泡(CO2を生成する水とポリイソシアナートの反応)及びゲル化(ポリオールとポリイソシアナートの反応)を加速するために用いられる。
本開示は、ポリウレタン材料の生成の触媒作用における使用のためのピロリジンに基づ
く触媒を提供する。
本発明を詳細に理解し且つより良く認識するために、添付の図と結び付けて以下の本発明の詳細な記載を参照するべきである。
本明細書に現れる場合、「含んでなる」という用語及びその派生語は、追加の成分、段階又は手順が本明細書に開示されていてもいなくても、それらの存在を排除することを意図していない。いずれの疑問をも避けるために、「含んでなる」という用語の使用を介して本明細書で特許請求されるすべての組成物は、そうでないと記載されていなければ、追加の添加物、助剤又は化合物を含むことができる。対照的に、「本質的に〜より成る」という用語は、本明細書に現れる場合、操作性に本質的でないもの以外の他の成分、段階又は手順を後に続く記述の範囲から排除し、「〜より成る」という用語は、用いられたら、特定的に記載されない又は挙げられない成分、段階又は手順を排除する。「又は」という用語は、他にことわれなければ、挙げられるメンバーを個々に、ならびにいずれかの組み合わせにおいて指す。
polyol”)は、1種のポリオール又は1種より多いポリオールを意味する。
式中、Rは:(CH2)n−R3、(CH2)n−OR3、(CH2)n−NR3COR4、(CH2)n−NR3SO2R4、(CH2)n−COOR3、(CH2)n−COR3、(CH2)n−SR3、(CH2)n−SOR3、(CH2)n−SO2R3、(CH2)n−SO3H、(CH2)n−SONR3R4及び(CH2)n−SO2NR3R4より成る群から選ばれ;
R3及びR4は独立して:
H;
場合によりハロゲン、ヒドロキシ、低級アルコキシ、N(低級アルキル)2、NCO、オキソ、カルボキシ、カルボキシ低級アルキル、シクロアルキル及びヘテロアリールで置換されていることができる低級アルキル;
場合によりハロゲン、低級アルコキシ、低級アルキル、カルボキシ、カルボキシ低級アルコキシ、カルボキシ低級アルキル、オキソ、CN、NCO及びNHSO2−低級アルキルで置換されていることができる低級シクロアルキル;
場合によりハロゲン、ヒドロキシ、NH2、NH−低級アルキル、NCO及びN−(低級アルキル)2で置換されていることができる低級アルケニル;
場合によりハロゲン、ヒドロキシ、NH2、NH−低級アルキル、NCO及びN−(低級アルキル)2で置換されていることができる低級アルキニル;
場合によりハロゲン、低級アルコキシ、低級アルキル、カルボキシ、カルボキシ低級アルコキシ、オキソ、NCO及びCNで置換されていることができる低級シクロアルケニル;場合によりハロゲン、低級アルコキシ、ヒドロキシ、低級アルキル、低級アルケニル、シクロアルキル、カルボキシ、カルボキシ低級アルコキシ、カルボキシ低級アルキル、オキソ、CN及びCONR5R6で置換されていることができるアリール;
場合によりハロゲン、低級アルコキシ、低級アルキル、カルボニル、カルボキシ、カルボキシ低級アルキル、カルボキシ低級アルコキシ、オキソ及びCNで置換されていることができるヘテロアリール;ならびに
場合によりハロゲン、低級アルキル、低級アルコキシ、カルボキシ、カルボキシ低級アルコキシ、オキソ、NCO、CN、SO2−低級アルキル及びオキソで置換された低級アルキルで置換されていることができる複素環
から選ばれ;そして
nは1〜6の整数である。
キル及びオキソで置換された低級アルキルで置換されていることができる複素環であり;そしてnは1〜6の整数である。さらなる態様において、本開示のピロリジンに基づく触媒はピロリジンプロパノール、1,1’−(オキシビス(エタン−2−1−ジイル)ジピロリジン)、2−ピロリジニル−1−(2−ピロリジニルエトキシ)エタン、2−(2−(ピロリジン−1−イル)エトキシ)エタン−1−オール、ピロリジニルブチル−モルホリン、ピロリジニルブチル−ピロリジン、イミノ−ビス−4−アミノブチルピロリジン及びそれらの混合物から選ばれる化合物である。
らにもっと別の態様において少なくとも10:1である。さらに別の態様において、式(I)のピロリジンに基づく触媒対少なくとも1個のアミン基を含有するアミン触媒及び/又は非アミン触媒の重量比は0.1:99.9〜99.9:0.1であり、さらに別の態様において1:99〜99:1であり、さらに別の態様において5:95〜95:5であり、さらなる態様において10:90〜90:10であるが、さらに別の態様において25:75〜75:25である。
第3級ホスフィン、例えばトリアルキルホスフィン及びジアルキルベンジルホスフィン;種々の金属のキレート、例えばアセチルアセトン、ベンゾイルアセトン、トリフルオロアセチルアセトン、エチルアセトアセテートなどと金属、例えばBe、Mg、Zn、Cd、Pd、Ti、Zr、Sn、As、Bi、Cr、Mo、Mn、Fe、Co及びNiから得られ得るもの;
金属カルボキシレート、例えば酢酸カリウム及び酢酸ナトリウム;
強酸の酸性金属塩、例えば塩化第二鉄、塩化第二錫、塩化第一錫、三塩化アンチモン、硝酸ビスマス及び塩化ビスマス;
強塩基、例えばアルカリ及びアルカリ土類金属水酸化物、アルコキシド及びフェノキシド;
種々の金属のアルコラート及びフェノラート、例えばR6がアルキル又はアリールであるTi(OR6)4、Sn(OR6)4及びAl(OR6)3ならびにアルコラートとカルボン酸、ベータ−ジケトン及び2−(N,N−ジアルキルアミノ)アルコールの反応生成物;
アルカリ土類金属、Bi、Pb、Sn又はAlカルボキシレート塩;ならびに
四価錫化合物及び三もしくは五価ビスマス、アンチモンもしくはヒ素化合物
が含まれる。
group)又は6〜15個の炭素原子を含有する芳香族炭化水素基である。
1,4−ジイソシアナート及びこれらの異性体の混合物;イソホロンジイソシアナート;2,4−及び2,6−ヘキサヒドロトルエンジイソシアナート及びこれらの異性体の混合物;ジシクロヘキシルメタン−4,4’−ジイソシアナート(水素化MDI又はHMDI);1,3−及び1,4−フェニレンジイソシアナート;2,4−及び2,6−トルエンジイソシアナート及びこれらの異性体の混合物(TDI);ジフェニルメタン−2,4’−及び/又は−4,4’−ジイソシアナート(MDI);ナフタレン−1,5−ジイソシアナート;トリフェニルメタン−4,4’,4”−トリイソシアナート;アニリンとホルムアルデヒドを縮合させ、続いてホスゲン化することにより得ることができる型のポリフェニル−ポリメチレン−ポリイソシアナート(粗MDI);ノルボルナンジイソシアナート;m−及びp−イソシアナトフェニルスルホニルイソシアナート;過塩素化アリールポリイソシアナート;カルボジイミド基、ウレタン基、アロファネート基、イソシアヌレート基、ウレア基又はビウレット基を含有する修飾ポリイソシアナート;テロメリゼーション反応により得られるポリイソシアナート;エステル基を含有するポリイソシアナート;ならびに高分子脂肪酸基を含有するポリイソシアナートが含まれるが、これらに限られない。当該技術分野における熟練者は、上記のポリイソシアナートの混合物を用いることも可能であることを認識するであろう。
には例えばスチレン又はアクリロニトリルが含まれる。ポリウレア改質ポリオールは、ポリオールの存在下におけるジアミンとジイソシアナートの反応により生成するポリウレア分散系を含有するポリオールである。ポリウレア改質ポリオールの変形は、ポリイソシアナートポリ付加(PIPA)ポリオール(polyisocyanate poly addition(PIPA) polyols)であり、それはポリオール中におけるイソシアナートとアルカノールアミンのその場反応により生成する。
。
oam)断熱材;衝突混合スプレーガン(impingement mix spray
guns)の使用を必要とする用途;ウレタン/ウレアハイブリッドエラストマー;自動車内部及び外部部品、例えばベッドライナー、ダッシュボード、ドアパネル及びハンドル;軟質フォーム(例えば家具用フォーム及び自動車部品フォーム);インテグラルスキンフォーム(integral skin foams);硬質スプレーフォーム;硬質現場注入発泡フォーム(pour−in place foams);コーティング;接着剤;シーラント;フィラメントワインディング;ならびに他のポリウレタン複合材料、フォーム、エラストマー、樹脂及び反応射出成形(RIM)用途において用いることができる。
ルアミンはジメチルシクロヘキシルアミンよりずっと弱い触媒であることが知られている。ブタノール中のジエチルシクロヘキシルアミンの場合のフェニルイソシアナートとの相対的な反応性は0.70であり、ジメチルシクロヘキシルアミンの場合、相対的な反応性は6.0である。相対的な反応性におけるこの向上は、立体障害のより小さい量の故である。ピロリジンに基づく触媒に関する相対的な反応性は、特に大きい量の立体障害を有する2−ピロリジニル−1−(2−ピロリジニルエトキシ)エタン触媒の場合、驚く程強い。
Claims (13)
- (i)ピロリジンプロパノール、1,1’−(オキシビス(エタン−2−1−ジイル)ジピロリジン)、2−ピロリジニル−1−(2−ピロリジニルエトキシ)エタン、2−(2−(ピロリジン−1−イル)エトキシ)エタン−1−オール、ピロリジニルブチルモルホリン、ピロリジニルブチルピロリジン、イミノ−ビス−4−アミノブチルピロリジン、1,3−ジピロリジノプロパン−2−オール及びそれらの混合物から選ばれるピロリジンに基づく触媒化合物;
(ii)イソシアナート官能基を含有する化合物;ならびに
(iii)活性水素含有化合物
を含んでなるポリウレタン調製物。 - イソシアナート官能基を含有する化合物がポリイソシアナート及びイソシアナート末端プレポリマーの少なくとも1つである請求項1のポリウレタン調製物。
- 活性水素含有化合物がポリオールである請求項1のポリウレタン調製物。
- ポリオールがポリアルキレンエーテルポリオール、ポリエステルポリオール、ポリマーポリオール、難燃性ポリオール、ハロゲン含有ポリオール又はそれらの混合物である請求項3のポリウレタン調製物。
- 少なくとも1個の第3級アミン基を含有するアミン触媒、非アミン触媒及びそれらの組合せから選ばれる少なくとも1つの追加の触媒をさらに含んでなる請求項1のポリウレタン調製物。
- アミン触媒がビス−(2−ジメチルアミノエチル)エーテル、N,N,N’−トリメチル−N’−ヒドロキシエチルビスアミノエチルエーテル、N−(3−ジメチルアミノプロピル)−N,N−ジイソプロパノールアミン、N,N−ジメチルエタノールアミン、トリエチレンジアミン、N,N−ジメチルエタノールアミンとトリエチレンジアミンのブレンド、N,N−ジメチルシクロヘキシルアミン、ベンジルジメチルアミン、ペンタメチルジエチレントリアミン、N,N,N’,N”,N”−ペンタメチルジプロピレントリアミン、N,N−ビス(3−ジメチルアミノプロピル)−N−イソプロパノールアミン、N’−(3−(ジメチルアミノ)プロピル−N,N−ジメチル)−1,3−プロパンジアミン、2−(2−ジメチルアミノエトキシ)エタノール、N,N,N’−トリメチルアミノエチルエタノールアミン、N−エチルモルホリン、N−メチルモルホリン、4−メトキシエチルモルホリン、2,2’ジモルホリノジエチルエーテル、1,3,5−トリス(3−(ジメチルアミノ)プロピル)ヘキサヒドロ−s−トリアジン、1−プロパンアミン,3−(2−(ジメチルアミノ)エトキシ)、置換イミダゾール、N,N’−ジメチルピペラジン、アミノエチルピペラジン、N,N’,N’−トリメチルアミノエチルピペラジン、ビス−(N−メチルピペラジン)ウレア、N−メチルピロリジン、2−アミノエチル−N−メチルピロリジン、ビス−(N−メチルピロリジン)エチルウレア、3−ジメチルアミノプロピルアミン、N,N,N”,N”−テトラメチルジプロピレントリアミン、テトラメチルグアニジン、N−メチルモルホリン、N−エチルモルホリン、N−ブチルモルホリン、ジモルホリノジエチルエーテル、N,N’−ジメチルアミノエタノール、N,N−ジメチルアミノエトキシエタノール、ビス−(ジメチルアミノプロピル)−アミノ−2−プロパノール、ビス−(ジメチルアミノ)−2−プロパノール、ビス−(N,N−ジメチルアミノ)エチルエーテル;N,N,N’−トリメチル−N’ヒドロキシエチル−ビス−(アミノエチル)エーテル、N,N−ジメチルアミノエチル−N’−メチルアミノエタノール、テトラメチルイミノビスプロピルアミン、反応性酸封鎖触媒及びそれらの混合物から選ばれる請求項5のポリウレタン調製物。
- ピロリジンに基づく触媒対少なくとも1つの追加の触媒の重量比が少なくとも1:1である請求項5のポリウレタン調製物。
- 気泡安定剤、界面活性剤、連鎖延長剤、顔料、充填剤、難燃剤、熱膨張性微小球、発泡剤、水、増粘剤、防煙剤、強化剤、酸化防止剤、UV安定剤、帯電防止剤、赤外線吸収剤、染料、離型剤、抗菌・カビ剤、殺生物剤及びそれらの組み合わせから選ばれる1種もしくはそれより多い補助成分をさらに含んでなる請求項1のポリウレタン調製物。
- ピロリジンプロパノール、1,1’−(オキシビス(エタン−2−1−ジイル)ジピロリジン)、2−ピロリジニル−1−(2−ピロリジニルエトキシ)エタン、2−(2−(ピロリジン−1−イル)エトキシ)エタン−1−オール、ピロリジニルブチルモルホリン、ピロリジニルブチルピロリジン、イミノ−ビス−4−アミノブチルピロリジン、1,3−ジピロリジノプロパン−2−オール及びそれらの混合物から選ばれるピロリジンに基づく触媒化合物の存在下で、イソシアナート官能基を含有する化合物、活性水素含有化合物及び場合により補助成分を接触させることを含んでなる、ポリウレタン材料の製造方法。
- 請求項9の方法に従って製造されるポリウレタン材料。
- ポリウレタン材料が硬質フォーム又は軟質フォームである請求項10のポリウレタン材料。
- ポリウレタン材料がDMF、ホルムアルデヒド及びジメチルアミンの少なくとも1つを実質的に含まない請求項10のポリウレタン材料。
- 下塗り、カーペット用の裏地材料、建築用複合材料、断熱材、スプレーフォーム断熱材、ウレタン/ウレアハイブリッドエラストマー;自動車内部及び外部部品中、軟質フォーム、インテグラルスキンフォーム、硬質スプレーフォーム;硬質現場注入発泡フォーム;コーティング;接着剤;シーラント又はフィラメントワインディングとしての使用のための請求項9の方法に従って製造されるポリウレタン材料。
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PCT/US2015/037304 WO2015200408A1 (en) | 2014-06-27 | 2015-06-24 | Pyrrolidine-based catalysts for use in polyurethane materials |
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CN111093825A (zh) * | 2017-09-14 | 2020-05-01 | 亨斯迈国际有限责任公司 | 含卤代烯烃的就地倾注聚氨酯隔热泡沫组合物 |
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